Hydrochloric Acid → HCID 73656618, compound

HRID 2249195Notes

Reaction equation

HRID 2249195 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][OH:13])([O-:5])=O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1.Cl>N1C=CC=CC=1>[OH:5][N:3]=[C:6]1[CH:11]=[CH:10][C:9](=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[C:23]#[N:24])[CH:8]=[C:7]1[CH2:12][OH:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 119232-Nitrobenzyl alcoholHCID 14797Potassium HydroxideHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 73656618HCID 73656618, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred and cooled (<15° C.) mixture of 134 parts of potassium hydroxide and 940 parts of pyridine were added portionwise 92 parts of 2-nitrobenzenemethanol. Next there were added 132.5 parts of 4-methoxybenzeneacetonitrile and stirring was continued for 4 hours at room temperature. The reaction mixture was diluted with 3000 parts of ice-water and the whole was acidified with 1270 parts of hydrochloric acid. The precipitate was filtered off, stirred overnight in methylbenzene and dried in vacuo at 60° C., yielding 128.8 parts (50.7%) of α-[4-(hydroxyimino)-3-(hydroxymethyl)-2,5-cyclohexadien-1-ylidene]-4-methoxybenzeneacetonitrile (interm. 40).

Workup

  1. temperaturecooled
  2. stirringstirring
  3. filtrationThe precipitate was filtered off
  4. stirringstirred overnight in methylbenzene
  5. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-7edeef94a53b45418dd7ce7bb4e65920
Source dataset
uspto-grants-1991_08
Patent number
US05043327

Reaction notes

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