HCID 19780396, compound → HCID 19780392, compound

HRID 2081707Notes

Reaction equation

HRID 2081707 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19]C)=[O:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([O-:3])=[O:2]>[OH-].[Na+].CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 19780396HCID 19780396, compound

Product 1

HCID 19780392HCID 19780392, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of the methyl ester (Example 32) (5.72 g) in 2N sodium hydroxide (35 ml) and methanol (140 ml) was heated under reflux for 6 hours. The reaction mixture was cooled and concentrated in vacuo. Acidification with aqueous hydrochloric acid and filtration gave 1-(3-nitrobenzyl)indoline-5-carboxylic acid, m.p. 259°-262° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. filtrationAcidification with aqueous hydrochloric acid and filtration

Sources & evidence

ORD record
ord-4e75637df9b545ee88da9e548c04a17e
Source dataset
uspto-grants-1993_02
Patent number
US05185361

Reaction notes

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