HCID 58118746, compound → HCID 58118798, compound

HRID 2197529Notes

Reaction equation

HRID 2197529 reaction equation
[F:1][C:2]1[C:8]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:6]=[C:5]([N+:14]([O-])=O)[C:3]=1[NH2:4]>C(O)C.[Ni]>[F:1][C:2]1[C:8]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:6]=[C:5]([NH2:14])[C:3]=1[NH2:4]

Participants

4

Reactant 1

HCID 58118746HCID 58118746, compound

Product 1

HCID 58118798HCID 58118798, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To a mixture of 2-fluoro-6-nitro-3-pyrrolidin-1-ylaniline (285 mg, 1.26 mmol) in ethanol (20 ml) was added a slurry of Raney nickel (approximately 100 mg) in ethanol. The mixture was stirred under a hydrogen atmosphere (1 atm) at rt overnight. The reaction was purged of hydrogen, flushed with nitrogen and then filtered through a pad of Celite® using ethanol to rinse. The filtrate was concentrated under reduced pressure to afford crude product (43 mg, 17%) which was used without purification. 1H NMR (300 MHz, DMSO-d6) 6.19 (dd, J=8.4, 1.5 Hz, 1H), 5.89 (dd, J=8.4, 8.4 Hz, 1H), 4.30 (s, 2H), 4.20 (s, 2H), 2.94-3.07 (m, 4H), 1.72-1.89 (m, 4H); ES-MS m/z 196.3 (MH)+; HPLC RT (Method B) 1.08 min.

Workup

  1. customThe reaction was purged of hydrogen
  2. customflushed with nitrogen
  3. filtrationfiltered through a pad of Celite®
  4. washto rinse
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-33f2801c0651400aa4dcc0fdd51372e1
Source dataset
uspto-grants-2012_12
Patent number
US08338594B2

Reaction notes

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