Sodium borohydride → HCID 18919703, compound

HRID 1290974Notes

Reaction equation

HRID 1290974 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[C:10]2/[C:11](=[O:21])[C:12]3[CH:13]=[C:14]([CH3:20])[CH:15]=[N:16][C:17]=3[CH2:18][CH2:19]/2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CC(O)C>[OH:21][CH:11]1[CH:10]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:19][CH2:18][C:17]2[N:16]=[CH:15][C:14]([CH3:20])=[CH:13][C:12]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18919705HCID 18919705, compound

Product 1

HCID 18919703HCID 18919703, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(E)-7,8-Dihydro-6-(4-methoxyphenyl)methylene-3-methylquinolin-5[6H]one (5 g, prepared according to Example 5) was suspended in IPA (20 ml) and sodium borohydride (1.5 g) was added. The mixture was heated at reflux for 3 hours and the solvent was then evaporated and the residue treated with 2N HCl. The acidic solution was washed with diethyl ether and was basified with solid sodium carbonate. The aqueous layer was extracted into ethyl acetate and the organic solution dried (MgSO4) and evaporated under reduced pressure. The residue was recrystallised from diisopropyl ether to give the title compound (4 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customthe solvent was then evaporated
  4. additionthe residue treated with 2N HCl
  5. washThe acidic solution was washed with diethyl ether
  6. extractionThe aqueous layer was extracted into ethyl acetate
  7. dry with materialthe organic solution dried (MgSO4)
  8. customevaporated under reduced pressure
  9. customThe residue was recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-31e602bff72e467f800b803ae92429dc
Source dataset
uspto-grants-1998_05
Patent number
US05753676

Reaction notes

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