Potassium Hydroxide → HCID 19087719, compound

HRID 1464278Notes

Reaction equation

HRID 1464278 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:23]3[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:24]=3[C:25]([O:27]C)=[O:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CO>[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:23]3[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:24]=3[C:25]([OH:27])=[O:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19087645HCID 19087645, compound

Product 1

HCID 19087719HCID 19087719, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of methyl 2-[N-{4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl}-N-ethoxycarbonylamino]-4-nitrobenzoate (1.58 g) in methanol (16 ml) was added 2N potassium hydroxide (5.0 ml). After stirring for 2 hours at 50° C., methanol was evaporated in vacuo. The residue was diluted with water, acidified with 3N hydrochloric acid, extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate, and evaporated. Crude 2-[N-{4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl}-N-ethoxycarbonylamino]-4-nitrobenzoic acid (1.57 g) was obtained as an amorphous.

Workup

  1. custommethanol was evaporated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e1135ceb32c649c89f72e044133714b2
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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