Methanol → HCID 13769188, compound

HRID 2232560Notes

Reaction equation

HRID 2232560 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([OH:19])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:27]([N:29]([CH2:33][CH3:34])[C:30](Cl)=[O:31])[CH3:28].CO>CN(C)C=O.C(O)C>[CH2:27]([N:29]([CH2:33][CH3:34])[C:30](=[O:31])[O:19][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1)[CH3:28]

Participants

7

Reactant 4

HCID 887MethanolHCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 178488407HCID 178488407, compound

Product 1

HCID 13769188HCID 13769188, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

The procedure is as in Example 37, starting with 3-(4-methoxyphenyl)-1-isoquinolinol (10 g), triethylamine (16 g) and diethylcarbamoyl chloride (21.7 g) in dimethylformamide (100 cc). After chromatograpy on silica gel, initially with a cyclohexane/ethyl acette (1:1 by volume) mixture and the second time with a tolune/methanol (98:2 by volume) mixture as eluants, and crysallization in 80% strength aqueous ethanol, 3-(4-methoxypenyl)-1-isoquinolyl diethylcarbamate (0.7 g), m.p. 84° C., is obtained.

Sources & evidence

ORD record
ord-0aef80746d974cbaa99798e81d108e86
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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