Methanol → HCID 178429214, compound

HRID 1607172Notes

Reaction equation

HRID 1607172 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].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=O)=[CH:16]1.CO>C(O)(=O)C>[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]3[NH:11][C:24]([C:17]4[C:18]5[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=5)[NH:15][CH:16]=4)=[N:1][C:2]=3[CH:3]=2)[NH:7][C:6]1=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 10256Indole-3-CarboxaldehydeHCID 135892372H-Indol-2-one, 5,6-diamino-1,3-dihydro-3,3-dimethyl-

Product 1

HCID 178429214HCID 178429214, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.1 g. 5,6-Diamino-3,3-dimethylindolin-2-one and 2.5 g. indole-3-aldehyde are stirred for 4 days at ambient temperature in 150 ml. methanol and 4 ml. glacial acetic acid. The solvent is then removed in a vacuum and the residue is purified by column chromatography on silica gel. The appropriate fractions are combined, the solvent is removed in a vacuum, the residue (3.7 g. of a yellow oil) is dissolved in methanol, dichloromethane added thereto until turbidity commences and then left to crystallise. There are obtained 3.1 g. of the title compound; m.p. 243°-245° C.

Workup

  1. customThe solvent is then removed in a vacuum
  2. customthe residue is purified by column chromatography on silica gel
  3. customthe solvent is removed in a vacuum
  4. dissolutionof a yellow oil) is dissolved in methanol
  5. additiondichloromethane added
  6. waituntil turbidity commences and then left
  7. customto crystallise
  8. customThere are obtained 3.1 g

Sources & evidence

ORD record
ord-c3c265e342b04e3fb3b4e2587bb4b0c1
Source dataset
uspto-grants-1989_09
Patent number
US04863945

Reaction notes

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