Water → HCID 18333017, compound

HRID 2269716Notes

Reaction equation

HRID 2269716 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[C:14](OC)=[O:15])([O-])=O.O>C(OCC)(=O)C.CO>[O:15]=[C:14]1[CH:13]([C:18]([O:20][CH3:21])=[O:19])[CH2:12][C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 277385MLS000737573HCID 4311764Sodium borohydride

Product 1

HCID 18333017HCID 18333017, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (1.10 g) was added to the mixed solution of dimethyl 2-[(2-nitrophenyl)methylidene]malonate (15.2 g) in ethyl acetate (50 ml) and methanol (200 ml) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes. Water was added to the mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. 5% Palladium-carbon (6.26 g) was added to the mixed solution of the residue in THF (100 ml) and methanol (100 ml), and catalytic hydrogenation was conducted at room temperature under atmospheric pressure for 3 days. The catalyst was removed by filtration, and the filtrate was concentrated. The obtained crude crystals were washed with a mixed solution of ethyl acetate/hexane=1/4 to give the entitled compound (9.487 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. addition5% Palladium-carbon (6.26 g) was added to the mixed solution of the residue in THF (100 ml)
  6. waitmethanol (100 ml), and catalytic hydrogenation was conducted at room temperature under atmospheric pressure for 3 days
  7. customThe catalyst was removed by filtration
  8. concentrationthe filtrate was concentrated
  9. customThe obtained crude crystals
  10. washwere washed with a mixed solution of ethyl acetate/hexane=1/4

Sources & evidence

ORD record
ord-d845509d33604ed2ba9cd5b9f59ce5f0
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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