Hydrochloric Acid → 3-carboethoxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 979365Notes

Reaction equation

[C:1]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:16][CH3:17])=[C:10]([O:14][CH3:15])[CH:11]=2)[CH2:6][N:5]1[CH3:18])([OH:3])=[O:2].Cl.[CH3:20][CH2:21]O>>[C:1]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:16][CH3:17])=[C:10]([O:14][CH3:15])[CH:11]=2)[CH2:6][N:5]1[CH3:18])([O:3][CH2:20][CH3:21])=[O:2]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 202022273-carboxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 202022163-carboethoxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

Procedure

The resulting tetrahydroisoquinoline derivative of formula 30 is then esterified with a suitable lower alkanol by standard means to produce a tetrahydroisoquinoline ester of formula 31 (step 2). For example, 3-carboxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (30) is treated with HCl in EtOH to produce 3-carboethoxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (31).

Sources & evidence

ORD record: ord-bf42ad28fbe24a24b6627674f3c9f47c
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04667038

Reaction notes

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