Formaldehyde → HCID 68132266, compound

HRID 268302Notes

Reaction equation

HRID 268302 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[CH2:13][NH:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[CH2:24]=O>C(O)=O>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[CH2:13][N:12]([CH3:24])[CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 68133610HCID 68133610, compound

Product 1

HCID 68132266HCID 68132266, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The free base released from 6.5 g. of rac.-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride is heated at 120°C. (bath temperature) for 1 hour with 10 ml. of formic acid and 10 ml. of 35% formalin solution. After evaporation, extraction with sodium carbonate solution and methylene chloride and acidification with ethanolic hydrogen chloride, there is obtained rac.-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline hydrochloride which is recrystallized from methanol-ether and then melts at 243°-246°C. (softening at 238°C). The free base melts at 115°-116°C. after recrystallization from ether-petroleum ether.

Workup

  1. customAfter evaporation, extraction with sodium carbonate solution and methylene chloride and acidification with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-b6ee6435c8e048a5900a8909b59d16f0
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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