Ammonia → HCID 21559931, compound

HRID 1578377Notes

Reaction equation

HRID 1578377 reaction equation
[NH2-].[Na+].N.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14][C:15]#N)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].ClC1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][CH:19]=1.[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[N:36]=[CH:35][CH:34]=[C:33]2Cl>>[CH2:14]([C:15]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][CH:19]=1)[C:8]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:6]([O:5][CH3:4])[CH:7]=1.[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[N:36]=[CH:35][CH:34]=[C:33]2[CH2:14][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:6]([O:5][CH3:4])[CH:7]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 24533Sodium amideHCID 667273,4-DimethoxybenzeneacetonitrileHCID 691404-ChloroquinolineHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 2

HCID 21559931HCID 21559931, compoundHCID 21559932HCID 21559932, compound

Procedure

The process of this invention utilizing sodium amide in liquid ammonia is effective in promoting the condensation of 3,4-dimethoxyphenylacetonitrile with 4-chloroquinoline and 6,7-dimethoxy-4-chloroquinoline to furnish 4-veratrylquinoline and 6,7-dimethoxy-4-veratrylquinoline, respectively, after hydrolysis. The process of U.S. Pat. No. 2,568,778 issued Sept. 25, 1951, utilizing sodium amide in benzene is ineffective in promoting these condensations.

Sources & evidence

ORD record
ord-f60e13f7536c432da0078378bfd068f0
Source dataset
uspto-grants-1976_02
Patent number
US03936461

Reaction notes

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