Chloroform → HCID 21285201, compound

HRID 2231936Notes

Reaction equation

HRID 2231936 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[C:11]([CH2:23][OH:24])[N:10]=2)[CH:6]=[CH:7][CH:8]=1.C(Cl)(Cl)Cl>C(N(CC)CC)C>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[C:11]([CH2:23][OH:24])[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 21285205HCID 21285205, compound2×

Product 1

HCID 21285201HCID 21285201, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 24.77 g (0.0676 M) of 1-(3-chlorophenyl)-3-(hydroxymethyl)-6,7-dimethoxy-isoquinoline hydrochloride (compound of Example 1), 150 ml of chloroform and 10.1 g (13.9 ml, 0.1 M) of triethylamine is refluxed for 15 minutes. After cooling the solution is extracted with 3×50 ml of water, the chloroform layer is dried over anhydrous sodium sulfate, evaporated, giving the aimed product in crystalline, base form. This base is purified by dissolving in 25 ml of hot 99.5% ethanol. After cooling the resulting crystalline mass is mixed with 25 ml of diethyl ether, cooled, filtered, washed with 3×5 ml of a mixture (1:1) of ethanol and ether, and subsequently dried at 60° to 80° C. Yield 16.73 g (75.1%), m.p. 118° to 120° C.

Workup

  1. temperatureis refluxed for 15 minutes
  2. temperatureAfter cooling the solution
  3. extractionis extracted with 3×50 ml of water
  4. dry with materialthe chloroform layer is dried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-e7fac2de88534de98ea6ad62a55889c2
Source dataset
uspto-grants-1988_11
Patent number
US04785104

Reaction notes

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