Dimethylformamide → HCID 21459166, compound

HRID 1781837Notes

Reaction equation

HRID 1781837 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-aea1dba770b54ddda72d118a6afff955
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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