Sodium borohydride → HCID 19968570, compound

HRID 975923Notes

Reaction equation

HRID 975923 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:15]([O-:17])=[O:16])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]#[N:14])=[CH:8][CH2:7][CH2:6]2.[BH4-].[Na+]>CCO.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:4]([N+:15]([O-:17])=[O:16])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]#[N:14])[CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 19968564HCID 19968564, compound

Product 1

HCID 19968570HCID 19968570, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-methoxy-5-nitro-3,4 -dihydronaphthalene-1-carbonitrile (0.41 g, 1.8 mmol) in 10 ml of EtOH was added NaBH4 (0.20 g, 5.3 mmol) and the resulting reaction mixture was stirred for 30 min at 25° C. The solvent was removed in vacuo to yield an oily residue which was dissolved in EtOAc and washed with brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to yield the desired product as a colorless oil (0.42 g, >95%) which was subjected to a following reaction without purification. 1H NMR (300 MHz, CDCl3):δ 1.86 (m, 2H), 2.04 (m, 2H), 2.62 (q, 2H, J=6.3 Hz), 3.83 (s, 3H), 4.17 (t, 1H, J=6.3 Hz), 7.10 (d, 1H, J=8.9 Hz), 7.45 (d, 2H, J=8.9 Hz).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was removed in vacuo
  3. customto yield an oily residue which
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f71952513f14e19b4f7ca65fc9b0349
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

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