Dimethylformamide → HCID 21459166, compound

HRID 2254750Notes

Reaction equation

HRID 2254750 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 552 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-437b17c0013b45cf9872c96d0878c6ed
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

Loading…