ChemicalBook CAS DataBase List 1,2,3,4-Tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid hydrochloride

1,2,3,4-Tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid hydrochloride synthesis

8synthesis methods

Product Name:1,2,3,4-Tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid hydrochloride
CAS Number:82586-62-7
Molecular formula:C12H16ClNO4
Molecular Weight:273.71

(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(tert-butyloxycarbonyl)-3-isoquinolinecarboxylic acid

358627-67-5
2 suppliers
inquiry

1,2,3,4-Tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid hydrochloride

82586-62-7
134 suppliers
$27.00/1g

Yield: 90.9%

Reaction Conditions:

with hydrogenchloride in methanol;water at 60; for 2 h;

Steps:

9
To a solution of (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(tert-butyloxycarbonyl)-3-isoquinolinecarboxylic acid (example 3) (60 g, 0.17 mol) in methanol (300 mL) was added 3 N aqueous HCl (240 mL, 0.72 mol). The mixture was heated to 60° C. and stirred at 60° C. for 2 hrs. The clear reaction solution was evaporated under vacuum to 200 mL. The resulting white suspension was then cooled to 0-5° C. and stirred at 0-5° C., filtered, and rinsed with cold water (2×35 mL). The solid was dried under vacuum to give 42 g of (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid hydrochloride (yield 90.9%, ee>98%). ¹H NMR (DMSO-d₆) δ: 3.06 (dd, J=16.7, 10.8 Hz, 1H, CHHCHCOOH), 3.22 (dd, J=16.7, 4.7 Hz, 1H, CHHCHCOOH), 3.72, 3.73 (s, 6 H, OCH₃), 4.21 (br s, 2H, CH₂N), 4.32 (dd, J=10.8, 4.7 Hz, 1H, CHCOOH), 6.85, 6.87 (s, 2H, PhH), 10.12 (br s, 2H, NHHCl).

References:

Brantford Chemicals Inc. US6642384, 2003, B1 Location in patent:Page/Page column 11

50-00-0 Synthesis