Ammonium formate → HCID 15895829, compound

HRID 428297Notes

Reaction equation

HRID 428297 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-])=O)[CH:15]=[CH:14][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])=[O:6].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:16]1[CH:15]=[CH:14][C:4]([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])=[O:6])=[C:3]([O:2][CH3:1])[CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18358116HCID 18358116, compound2×

Product 1

HCID 15895829HCID 15895829, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methoxy-2′-methyl-4-(2-nitrophenylamino)benzophenone (Compound 255, 1.02 g, 2.8 mmol) in methanol (10 ml) was added, under argon, ammonium formiate (0.80 g, 13 mmol) and 10% palladium on carbon (0.16 g). The reaction mixture was stirred at room temperature for 16 hours. The mixture was filtered through Celite® and evaporated in vacuo. The residue was treated with water (50 ml) and extracted with methylene chloride (2×50 ml). The organic phase was dried (MgSO4), filtered and evaporated in vacuo to afford the crude product which was further purified by chromatography using ethyl acetate/pentane 1:1 as eluant.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customevaporated in vacuo
  3. additionThe residue was treated with water (50 ml)
  4. extractionextracted with methylene chloride (2×50 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-e3d3967434c345aabfc349453c5319c8
Source dataset
uspto-grants-2001_11
Patent number
US06313174B1

Reaction notes

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