Ammonium formate → HCID 67223501, compound

HRID 1947642Notes

Reaction equation

HRID 1947642 reaction equation
[CH2:1]([N:3]1[CH2:12][C:11]([CH3:14])([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-])=O)=[CH:8][CH:9]=2)[C:4]1=[O:18])[CH3:2].C([O-])=O.[NH4+]>CN(C=O)C.[Pd]>[NH2:15][C:7]1[CH:6]=[C:5]2[C:10]([C:11]([CH3:13])([CH3:14])[CH2:12][N:3]([CH2:1][CH3:2])[C:4]2=[O:18])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67223823HCID 67223823, compound

Product 1

HCID 67223501HCID 67223501, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium/Carbon (10% wt) (12 mg, 0.04 mmol) was added to a stirred solution of 2-ethyl-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one (110 mg, 0.44 mmol) and ammonium formate (137 mg, 2.21 mmol) in anhydrous DMF (6 ml) at room temperature. The resulting suspension was heated at reflux for lhr, then cooled and filtered through a pad of celite. The solvent was evaporated in vacuo and the crude residue purified by flash column chromatography (60% ethyl acetate in dichloromethane) to afford the title compound as a pale yellow solid (40 mg, 98%). HPLC retention time 2.99 min. Mass spectrum (ES+) m/z 219 (M+H).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for lhr
  3. temperaturecooled
  4. filtrationfiltered through a pad of celite
  5. customThe solvent was evaporated in vacuo
  6. customthe crude residue purified by flash column chromatography (60% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-38bbc24127a94e05a8381c4be67a94a7
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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