HCID 19042271, compound → HCID 19042264, compound

HRID 1684269Notes

Reaction equation

HRID 1684269 reaction equation
[C:1]([NH:4][C:5]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:6]=1[O:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=1[F:20])(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pt]>[C:1]([NH:4][C:5]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:6]=1[O:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[F:20])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 19042271HCID 19042271, compound

Product 1

HCID 19042264HCID 19042264, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of nitro compound 15 (1.0 g, 3.1 mmol) in ethyl acetate (20 mL) and Pt/C (200 mg) was stirred for 2 hrs under H2 (1 atm). The reaction mixture was filtered through Celite and concentrated under reduced pressure. The crude product was recrystalized with benzene providing amino ethane 16 as a white solid (709 mg, 78%), m.p. 134°-136° C. 1H NMR (CDCl3): 2.12 (s, 3H), 4.29 (s, 4H) (s, 4H), 6.4-6.3 (m, 1H), 6.46 (dd, J=12.5, 2.5 Hz, 1H), 6.7-6.6 (m, 2H), 6.85 (dd, J=9, 9 Hz, 1H), 8.30 (dd, J=9, 6 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was recrystalized with benzene

Sources & evidence

ORD record
ord-4100216001014464a68150268ded1bfb
Source dataset
uspto-grants-1997_06
Patent number
US05639906

Reaction notes

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