Methyl 4-pyridylacetate → HCID 178429216, compound

HRID 979209Notes

Reaction equation

HRID 979209 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[N:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](OC)=O)=[CH:17][CH:16]=1>>[OH2:12].[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]3[NH:11][C:22]([CH2:21][C:18]4[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=4)=[N:1][C:2]=3[CH:3]=2)[NH:7][C:6]1=[O:12]

Participants

3

Reactant 2

HCID 122482Methyl 4-pyridylacetateHCID 135892372H-Indol-2-one, 5,6-diamino-1,3-dihydro-3,3-dimethyl-

Product 1

HCID 178429216HCID 178429216, compound

Procedure

A suspension of 7.3 g. (0.038 mol) 5,6-diamino-3,3-dimethylindolin-2-one in 11.6 g. (0.077 mol) methyl 4-pyridylacetate is heated, while stirring, under an atmosphere of nitrogen for about 16 hours to 180° C. Subsequently, excess ester is distilled off in a vacuum and the residue obtained is separated on silica gel (elution agent: dichloromethane/ammonia-saturated methanol 20:1 v/v). Yield: 1.8 g. (16% of theory); m.p. 333°-337° C. (recrystallised from water/methanol 10:1 v/v).

Workup

  1. additionA suspension of 7.3 g
  2. distillationSubsequently, excess ester is distilled off in a vacuum
  3. customthe residue obtained
  4. customis separated on silica gel (elution agent: dichloromethane/ammonia-saturated methanol 20:1 v/v)
  5. customm.p. 333°-337° C. (recrystallised from water/methanol 10:1 v/v)

Sources & evidence

ORD record
ord-192784c193a14dda9301ba051da2f375
Source dataset
uspto-grants-1987_05
Patent number
US04666923

Reaction notes

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