Benzaldehyde → HCID 178473795, compound

HRID 1607173Notes

Reaction equation

HRID 1607173 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:14])=[C:10]([NH2:13])[CH:11]=2)[C:6]([CH3:16])([CH3:15])[CH2:5]1)(=[O:3])[CH3:2].CO.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[O-2].[O-2].[Mn+4].C(O)(=O)C>[C:1]([N:4]1[C:12]2=[CH:11][C:10]3[NH:13][C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:14][C:9]=3[CH:8]=[C:7]2[C:6]([CH3:16])([CH3:15])[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 887MethanolHCID 14183251HCID 14183251, compound

Product 1

HCID 178473795HCID 178473795, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2.2 g. (10 mmole) 1-acetyl-5,6-diamino-3,3-dimethylindoline, 200 ml. methanol, 5.2 ml. acetic acid, 1.0 ml. benzaldehyde and 50 mg. manganese dioxide is stirred for 3 hours at ambient temperature while passing in air. The reaction mixture is then filtered, the filtrate evaporated and the residue chromatographed on silica gel. After evaporation of the appropriate fractions and trituration with diethyl ether, there is obtained 0.8 g. (26% of theory) of the title compound; m.p. 225°-227° C.

Workup

  1. additionA mixture of 2.2 g
  2. filtrationThe reaction mixture is then filtered
  3. customthe filtrate evaporated
  4. customthe residue chromatographed on silica gel
  5. customAfter evaporation of the appropriate fractions and trituration with diethyl ether
  6. customthere is obtained 0.8 g

Sources & evidence

ORD record
ord-0626c7b84f0048a48d524b7ebf1e5180
Source dataset
uspto-grants-1989_09
Patent number
US04863945

Reaction notes

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