HCID 53684638, compound → HCID 14535919, compound

HRID 2351860Notes

Reaction equation

HRID 2351860 reaction equation
CN(C)[CH:3]=[CH:4][C:5]1[C:10]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=[CH:7][C:6]=1[N+:21]([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:5]=2[CH:4]=[CH:3][NH:21]3)=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 53684638HCID 53684638, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14535919HCID 14535919, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 32 g. (0.098 mole) of 2-(2-dimethylaminoethenyl)-3-(4-methoxybenzoyl)nitrobenzene in 200 ml of ethyl acetate was treated with 5 g of 10% palladium-on-charcoal, and the starting material reduced with hydrogen under 50 p.s.i.g. The mixture was then filtered, the filtrate taken to dryness, and the residue recrystallized from ethyl acetate to give 18.1 g of 4-(4-methoxybenzoyl)indole. Another sample, similarly prepared by reduction of the starting material with Raney nickel in ethanol, afforded material having m.p. 148°-152° C. Anal., Calc. for C15H11NO: C, 76.48; H, 5.21; N, 5.57. Found: C, 76.73; H, 5.27; N, 5.58.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fd855bb238dd481aabb65eca86e60f0a
Source dataset
uspto-grants-1989_10
Patent number
US04874761

Reaction notes

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