2-Methoxyethanol → HCID 19816018, compound

HRID 2247894Notes

Reaction equation

HRID 2247894 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:19]([O-])=O)=[C:13]([CH:18]=1)[C:14]([NH:16][CH3:17])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1C=CC=C1.COCCO.[H][H]>CO.[Pd]>[NH2:19][C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:18][C:13]=1[C:14]([NH:16][CH3:17])=[O:15]

Participants

7

Reactant 4

HCID 80192-MethoxyethanolHCID 8030ThiopheneHCID 19816068HCID 19816068, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19816018HCID 19816018, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6.5 parts of intermediate 21, namely 5-benzoyl-N-methyl-2-nitrobenzamide, 2 parts of a solution of thiophene in methanol 4% and 97 parts of 2-methoxyethanol was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was recrystallized from 2-propanol, yielding 4.64 parts (79.3%) of 2-amino-5-benzoyl-N-methylbenzamide; mp. 140.5° C. (interm. 22).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-03207340a5c648ada709f6e94affbff8
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

Loading…