H-DL-TIC-OH Chemical Properties

Melting point:

358°C

Boiling point:

372.0±42.0 °C(Predicted)

Density 

1.225±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Sodium Hydroxide, Water

form 

Solid

pka

2.21±0.20(Predicted)

color 

White

CAS DataBase Reference

67123-97-1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

HS Code 

2933499090

H-DL-TIC-OH Usage And Synthesis

Chemical Properties

White Solid

Uses

rac 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid (cas# 67123-97-1) is a compound useful in organic synthesis.

Synthesis

D,L-phenylalanine (50 g, 3.03 mol) was used as raw material to prepare its suspension. Concentrated hydrochloric acid (325 mL) and 37% formaldehyde solution (110 mL) were added to the suspension under vigorous stirring and heated to a mild reflux condition and maintained for 30 min. Subsequently, additional formaldehyde (50 mL) and concentrated hydrochloric acid (110 mL) were added and the reaction continued to heat for 4 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and the solid product was collected by filtration. The solid was washed with methanol (30 mL) and dried to afford the target compound 3-carboxy-1,2,3,4-tetrahydroisoquinoline in a yield of 64.09 g (98.9% yield) with a melting point of 295-298 °C (decomposition temperature >326 °C) (Literature reference: Julian PL, J. Chem. Soc. 1948, 70, 180-183) as an enantiomeric mixtures. Its NMR hydrogen spectrum (DMSO-d6) data are as follows: δ 3.10-3.18 (1H, m, CH), 3.28-3.34 (1H, m, CH), 4.27 (2H, s, CH2), 4.39 (1H, m, CH), 7.25-7.27 (4H, m, 4*ArH), 9.89 (1H, brs, exchangeable, NH) , 10.06 (1H, brs, exchangeable, OH). Mass spectral data: m/z 177.0 (M+H)+.

References

[1] Patent: US2009/117125, 2009, A1. Location in patent: Page/Page column 15
[2] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 12, p. 3729 - 3731
[3] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1325 - 1344
[4] Journal of the American Chemical Society, 1948, vol. 70, p. 180,182
[5] Journal of Organic Chemistry, 1951, vol. 16, p. 430

H-DL-TIC-OH(67123-97-1)Related Product Information

• 1,2,3,4-TETRAHYDROISOQUINOLINE
• Isoquinoline-1-carboxylic acid
• Quinapril
• (S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid hydrobromide
• H-DL-TIC-OH
• Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt
• (S)-6,7-Dimethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrochloride
• Quinapril benzyl ester maleate
• Quinapril hydrochloride
• (S)-6,7-Dimethoxy-1,2,3,3-tetrahydro-2-isoquinolinecarboxylic acid hydrochloride
• L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid