Sodium borohydride → HCID 12016896, compound

HRID 1531434Notes

Reaction equation

HRID 1531434 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][C:8]([N+:12]([O-:14])=[O:13])=[CH:7]2.[BH4-].[Na+]>C(Cl)(Cl)Cl.C(O)(C)C>[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-:14])=[O:13])[CH2:7]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11845284HCID 11845284, compound

Product 1

HCID 12016896HCID 12016896, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

8-Fluoro-3-nitro-2H-1-benzopyran-5-carboxamide (730 mg, 3.1 mmol) was slurried in chloroform (75 mL) and isopropyl alcohol (25 mL). To the stirred mixture, silica gel (2.2 g, 230-400 mesh ASTM) was added followed by powdered sodium borohydride (255 mg, 6.2 mmol) portionwise over a period of 15 min. After the addition was complete, the reaction was stirred for 20 min. and the reaction was then quenched by the addition of acetic acid (2 mL) and stirred for an additional 30 min. The insoluble material was filtered off and the solvent removed in vacuo. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate, the combined ethyl acetate phases were treated with brine, dried with MgSO4, filtered, and the solvent was removed in vacuo to give 0.67 g (91% yield) of an off-white solid as the title compound (mp 191.0-191.5° C.). EIMS (70 eV) m/z (relative intensity) 240 (1, M+), 195 (17), 194 (100), 193 (17), 177 (26), 151 (44), 149 (27), 148 (18), 123 (23), 103 (48), 102 (11), 101 (29), 96 (13), 95 (15), 94 (11), 88 (41), 83 (14), 77 (25), 76 (11), 75 (39), 74(23), 70 (10), 63 (11), 60 (11), 51 (17), 50 (10).

Workup

  1. additionTo the stirred mixture, silica gel (2.2 g, 230-400 mesh ASTM) was added
  2. additionAfter the addition
  3. customthe reaction was then quenched by the addition of acetic acid (2 mL)
  4. stirringstirred for an additional 30 min
  5. filtrationThe insoluble material was filtered off
  6. customthe solvent removed in vacuo
  7. customThe residue was partitioned between ethyl acetate and water
  8. extractionThe aqueous phase was extracted with ethyl acetate
  9. additionthe combined ethyl acetate phases were treated with brine
  10. dry with materialdried with MgSO4
  11. filtrationfiltered
  12. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-01fb2c84f3f54e7bbe57dd056185a1bf
Source dataset
uspto-grants-2001_03
Patent number
US06197978B1

Reaction notes

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