Dimethylformamide → 2-(4-Hydroxy-3-methoxy-5-nitrobenzoyl)-3-methylindole

HRID 1781819Notes

Reaction equation

HRID 1781819 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]([O:15][CH3:16])[CH:6]=1)=[O:4].N[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.C[N:28](C)C=O>>[OH:14][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([C:3]([C:2]2[NH:28][C:26]3[C:21]([C:19]=2[CH3:18])=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:4])=[CH:6][C:7]=1[O:15][CH3:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11952PhenacylamineHCID 144509832-Bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone

Product 1

HCID 214589792-(4-Hydroxy-3-methoxy-5-nitrobenzoyl)-3-methylindole

Procedure

ac) A solution of 29.0 g of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone and 13.5 g of 2-aminoacetophenone in 250 ml of dry N,N-dimethylformamide is stirred at 90° for 16 hours. The reaction mixture is then evaporated to about two thirds and poured on to ice. The separated crystals are filtered under suction and dissolved in methylene chloride. The solution is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. There is obtained 2-(4-hydroxy-3-methoxy-5-nitrobenzoyl)-3-methylindole of m.p. 195°-197° (from methylene chloride/methanol).

Workup

  1. customThe reaction mixture is then evaporated to about two thirds
  2. additionpoured on to ice
  3. filtrationThe separated crystals are filtered under suction
  4. dissolutiondissolved in methylene chloride
  5. washThe solution is washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-03b7bd662d1a4889abc766e94fc0d239
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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