Thiophene → HCID 19816065, compound

HRID 2247907Notes

Reaction equation

HRID 2247907 reaction equation
[CH3:1][O:2][CH:3]([O:21][CH3:22])[C:4]1[CH:5]=[C:6]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O.S1C=CC=C1.[O-2].[Ca+2]>CO.[Pd]>[NH2:10][C:9]1[CH:8]=[CH:7][C:6]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])=[CH:5][C:4]=1[CH:3]([O:2][CH3:1])[O:21][CH3:22]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 6850728CalciumoxideHCID 19816024[3-(Dimethoxymethyl)-4-nitrophenyl]phenylmethanone

Product 1

HCID 19816065HCID 19816065, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 68 parts of intermediate 10, namely [3-(dimethoxymethyl)-4-nitrophenyl] phenylmethanone, 4 parts of a solution of thiophene in methanol 4%, 20 parts of calcium oxide and 474 parts of methanol was hydrogenated for 24 hours at normal pressure and room temperature with 6 parts of palladium-on-charcoal catalyst 10%. The catalyst was filtered off and the filtrate was evaporated. The residue was co-evaporated with methylbenzene, yielding 59.1 parts (96.8%) of [4-amino-3-(dimethoxymethyl)phenyl] phenylmethanone (interm. 64).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c41aefa104314cd4b5c8772b4bf5b422
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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