Ethanol → 3-amino-8-fluorochromane-5-carboxamide

HRID 1531435Notes

Reaction equation

HRID 1531435 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]([NH2:17])=[O:16])=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]([N+:12]([O-])=O)[CH2:7]2.C(O)C>O1CCCC1.[Ni]>[NH2:12][CH:8]1[CH2:7][C:6]2=[C:5]([C:15]([NH2:17])=[O:16])[CH:4]=[CH:3][C:2]([F:1])=[C:11]2[O:10][CH2:9]1

Participants

5

Reactant 2

HCID 702EthanolHCID 12016896HCID 12016896, compound

Product 1

HCID 118454513-amino-8-fluorochromane-5-carboxamideYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

8-Fluoro-3-nitro-3,4-dihydro-2H-1-benzopyran-5-carboxamide (9.0 g, 37.5 mmol), dissolved in tetrahydrofuran (100 mL) and absolute ethanol (400 mL), was subjected to atmospheric hydrogenation conditions using Raney nickel (W-2, 9 g) at room temperature. The reaction was complete after 48 hours, at which time the catalyst was filtered off, washed with hot ethanol and the combined solvents were removed in vacuo to give 7.8 g (99% yield) of an off-white solid. A portion was recrystallized from ethyl acetate to give white crystals as the title compound (mp 187-188° C). EIMS (70 eV) m/z (relative intensity) 210 (6, M+), 194 (30), 193 (100), 192 (20), 178 (12).

Workup

  1. customat room temperature
  2. filtrationthe catalyst was filtered off
  3. washwashed with hot ethanol
  4. customthe combined solvents were removed in vacuo

Sources & evidence

ORD record
ord-0b6c131aa6354d22bc71194fa4111dad
Source dataset
uspto-grants-2001_03
Patent number
US06197978B1

Reaction notes

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