Acetic Acid → HCID 70510514, compound

HRID 1707122Notes

Reaction equation

HRID 1707122 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-:26])=[O:25])[CH2:9][C:10]3([CH2:15][CH2:14][N:13](C#N)[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.C(O)(=O)C.[OH-].[Na+].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>Cl.CCOCC>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-:26])=[O:25])[CH2:9][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 444266Maleic AcidHCID 128016286-Chloro-1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

Product 1

HCID 70510514HCID 70510514, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 2.5 g of 6-chloro-1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine], Example 31, in 40 ml of 3 N hydrochloric acid and 20 ml of glacial acetic acid is refluxed for 16 hours under nitrogen. Thereafter, the mixture is permitted to cool before sequentially being basified with dilute sodium hydroxide and extracted with ether. The combined ether extracts are successively washed with water, dried and concentrated under vacuum leaving an oil residue. The residue, in ether, is converted to its maleic acid salt which is recrystallized from an acetone-ether mixture to provide orange prisms, mp 153°-155° C. of 6-chloro-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine] maleate.

Workup

  1. temperatureto cool
  2. extractionextracted with ether
  3. washThe combined ether extracts are successively washed with water
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customleaving an oil residue
  7. customis recrystallized from an acetone-ether mixture

Sources & evidence

ORD record
ord-d0df6a0c6ae6448596a5a22127a0921e
Source dataset
uspto-grants-1980_06
Patent number
US04209625

Reaction notes

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