Dimethylformamide → HCID 21459166, compound

HRID 2260249Notes

Reaction equation

HRID 2260249 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([OH:15])[CH:6]=1)=[O:4].N[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O.C[N:27](C)C=O>>[OH:15][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]=1[OH:14])[C:3]([C:2]1[NH:27][C:25]2[C:20]([C:18]=1[CH3:17])=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:4]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11952PhenacylamineHCID 218455962-Bromo-1-(3,4-dihydroxy-5-nitro-phenyl)-ethanone

Product 1

HCID 21459166HCID 21459166, compound

Procedure

A solution of 5.52 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone and 2.7 g of 2-aminoacetophenone in 100 ml of dry N,N-dimethylformamide is stirred at 90° for 24 hours. The reaction mixture is evaporated, the residue is dissolved in ethyl acetate, washed with water, dried over sodium sulfate, filtered and evaporated. There is obtained 2-(3,4-dihydroxy-5-nitrobenzoyl)-3-methylindole of m.p. 212°-214° (from n-butanol).

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-096cc64d282b418fa3e5f73a19e123a3
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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