Sodium borohydride → HCID 10198426, compound

HRID 362882Notes

Reaction equation

HRID 362882 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4](=[O:16])[CH2:5]/[C:6]/2=[CH:12]\[C:13]([NH2:15])=[O:14].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]([OH:16])[CH2:5]/[C:6]/2=[CH:12]\[C:13]([NH2:15])=[O:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15896151HCID 15896151, compound

Product 1

HCID 10198426HCID 10198426, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (E)-2-(4,6-difluoro-3-oxo-1-indanylidene)acetamide (0.100 g, 0.45 mmol) and sodium borohydride (0.017 g, 0.45 mmol) in 95% ethanol was stirred at ambient temperature for 2 hours. The mixture was cooled in an ice bath and quenched with 0.1N hydrochloric acid (3 mL). The ethanol was evaporated in vacuo, and the residue was dissolved in ethyl acetate (50 mL), washed successively with water (2×3 mL) and brine (30 mL), dried over sodium sulfate, filtered, and evaporated in vacuo. The resudue was washed successively with cold ethyl acetate, hexane, and diethyl ether to give 0.046 g (45%) of (E)-2-(4,6difluoro-3-hydroxy-1-indanylidene)acetamide as a white solid; mp 232°-237° C. (dec.) 1H-NMR (DMSO-d6): δ7.06-7.42 (m, 4H), 6.49 (s, 1H), 5.52 (d, 1H), 5.30 (m,1H), 3.44 (m,1H), 3.03 (d, 1H).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customquenched with 0.1N hydrochloric acid (3 mL)
  3. customThe ethanol was evaporated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  5. washwashed successively with water (2×3 mL) and brine (30 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. washThe resudue was washed successively with cold ethyl acetate, hexane, and diethyl ether

Sources & evidence

ORD record
ord-b521bca281dc433c8faf0047c1c09a90
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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