HCID 59442072, compound → HCID 16787689, compound

HRID 1014232Notes

Reaction equation

HRID 1014232 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[CH2:10][N:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[N+:15]([O-])=O>C(O)C.[Pd]>[NH2:15][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:14])[CH2:10][N:11]([CH3:12])[CH3:13])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 59442072HCID 59442072, compound

Product 1

HCID 16787689HCID 16787689, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N1-(4-fluoro-3-nitrophenyl)-N2,N2-dimethylglycinamide (3.0 g, 12.4 mmol) , 10% Pd/C (˜0.500 g, Lancaster) in absolute ethanol (100 mL) was stirred under 50 psi H2(g) overnight. The catalyst was removed by vacuum filtration through a celite pad, rinsed with methanol, and the filtrate was concentrated under reduced pressure to give N1-(3-amino-4-fluorophenyl)-N2,N2-dimethylglycinamide (2.23 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.22 (s, 6 H) 2.97 (s, 2 H) 5.09 (s, 2 H) 6.64 (ddd, J=8.74, 3.98, 2.66 Hz, 1 H) 6.83 (dd, J=11.26, 8.70 Hz, 1 H) 7.15 (dd, J=8.42, 2.56 Hz, 1 H) 9.40 (s, 1 H).

Workup

  1. customThe catalyst was removed by vacuum filtration through a celite pad
  2. washrinsed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-63736d0d32db4911b5e8f65b9bf3f2bb
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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