Lithium borohydride → 4-[1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-2-hydroxy-ethylamino]-benzonitrile

HRID 993131Notes

Reaction equation

HRID 993131 reaction equation
C[O:2][C:3](=O)[CH:4]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:16][C:15]=1[N+:30]([O-:32])=[O:31])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][CH:7]=1.[BH4-].[Li+]>C(COC)OC>[CH2:23]([O:22][C:17]1[C:18]([O:20][CH3:21])=[CH:19][C:14]([CH:4]([NH:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]#[N:13])=[CH:10][CH:11]=2)[CH2:3][OH:2])=[C:15]([N+:30]([O-:32])=[O:31])[CH:16]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 22890463(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-(4-cyano-phenylamino)-acetic acid methyl ester

Product 1

HCID 228904544-[1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-2-hydroxy-ethylamino]-benzonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-(4-cyano-phenylamino)-acetic acid methyl ester (4.5 g, 10 mmole) was dissolved in dimethoxyethane and lithium borohydride (0.210 g, 10 mmole) added. The reaction was heated to reflux for three hours and cooled to room temperature. The reaction was quenched with water containing acetic acid and diluted with ethyl acetate. After transferring to a separatory funnel, the organic layer was washed with water several times. The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent removed. The crude material was then submitted to flash chromatography to yield 3.1 g of 4-[1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-2-hydroxy-ethylamino]-benzonitrile (74%). 1HNMR(CDCl3):7.77 (s, 1H), 7.3-7.5 (m, 7H), 7.15 (s, 1H), 6.42 (d, 2H), 5.4 (bs, 1H), 5.18 (dd AB syst., 2H), 4.15 (dd, 1H), 3.83 (s, 3H), 3.79-3.86 (dd, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for three hours
  3. customThe reaction was quenched with water
  4. additioncontaining acetic acid
  5. additiondiluted with ethyl acetate
  6. customAfter transferring to a separatory funnel
  7. washthe organic layer was washed with water several times
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed

Sources & evidence

ORD record
ord-58ede6e010ce49b7adfd0a152fc2179d
Source dataset
uspto-grants-2002_10
Patent number
US06472393B1

Reaction notes

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