2-Amino-5-methoxybenzoic acid Chemical Properties

Melting point:

148-152 °C

Boiling point:

349.9±27.0 °C(Predicted)

Density 

1.303±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Methanol (Slightly)

form 

Crystalline Powder

pka

2.08±0.10(Predicted)

color 

White to yellow to pale orange

BRN 

777690

InChI

InChI=1S/C8H9NO3/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4H,9H2,1H3,(H,10,11)

InChIKey

UMKSAURFQFUULT-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(OC)=CC=C1N

CAS DataBase Reference

6705-03-9(CAS DataBase Reference)

NIST Chemistry Reference

5-Methoxyanthranilic acid(6705-03-9)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36/37/39-36-37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29225090

MSDS

• Language:English Provider:ALFA

2-Amino-5-methoxybenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Amino-5-methoxybenzoic acid is a general reagent used in the synthesis of substituted isoquinolinonaphthyridines, quinazolinones, imidazobenzodiazepines, pyridoquinazolones and polycyclic hexahydrobenzo[c]acridines.

Uses

2-Amino-5-methoxybenzoic Acid is used in the synthesis of quinazolinone class of histamine H3 receptor inverse agonists. It is also used in the synthesis of Alogliptin, a selective inhibitor of the s erine protease dipeptidyl peptidase IV.

Definition

ChEBI: 2-Amino-5-methoxybenzoic acid is a methoxybenzoic acid.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Using 5-methoxy-2-nitrobenzoic acid (1) as starting material, its nitro group was reduced by catalytic hydrogenation using H2 and Pd/C to afford 2-amino-5-methoxybenzoic acid (2) in quantitative yield. Subsequently, compound (2) was subjected to diazotization reaction with NaNO2 followed by treatment with Na2S2 to obtain stable disulfide compound (3) in 80% yield. This disulfide (3) was directly reacted with SOCl2 without further purification, followed by reaction with 2-chloroethylamine in the presence of Et3N to produce amide (4) in 90% yield. The compound (4) was converted to the cyclized product (5) by a one-pot method with trimethylphosphine and Et3N co-refluxed in THF. Finally, reduction of the cyclized amide (5) using LiAlH4 afforded 7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (6).

References

[1] Patent: US2007/49572, 2007, A1. Location in patent: Page/Page column 34
[2] Patent: US2005/215540, 2005, A1. Location in patent: Page/Page column 37
[3] Patent: WO2016/23826, 2016, A1. Location in patent: Page/Page column 40
[4] Synthesis (Germany), 2017, vol. 49, # 1, p. 135 - 144
[5] Medicinal Chemistry Research, 2002, vol. 11, # 9, p. 504 - 537

2-Amino-5-methoxybenzoic acid (6705-03-9)Related Product Information

• 4-Aminobenzoic acid
• 3,4-Dimethoxybenzoic acid
• 2-Amino-5-methylbenzoic acid
• ALTRENOGEST
• (Trifluoromethoxy)benzene
• 2-BROMO-5-METHOXYBENZOIC ACID
• 2,6-Dimethoxybenzoic acid
• 4-Dimethylaminobenzoic acid
• Glycine
• Tris(hydroxymethyl)aminomethane
• D-ribo-Hexanoic acid, 3-deoxy-, γ-lactone
• Methyl 2-amino-3,4,5-trimethoxybenzoate
• Anthranilic acid
• ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE
• 2-AMINO-3,4,5-TRIMETHOXYBENZOIC ACID
• Methyl 2-nitro-3,4,5-trimethoxybenzoate
• 2-Amino-4,5-dimethoxybenzoic acid
• Bifenox