Sodium borohydride → (2-Amino-5-chlorophenyl)(3-methoxyphenyl)methanol

HRID 747599Notes

Reaction equation

HRID 747599 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)=[O:10].[BH4-].[Na+]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12325894(2-Amino-5-chlorophenyl)(3-methoxyphenyl)methanone

Product 1

HCID 57777837(2-Amino-5-chlorophenyl)(3-methoxyphenyl)methanolYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3.66 g of (2-amino-5-chlorophenyl)(3-methoxyphenyl)methanone dissolved in 15 ml of ethanol are added, at 20° C., 1.59 g of sodium borohydride. After 24 hours at 20° C., the reaction medium is concentrated, taken up in ethyl acetate and washed twice with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is solidified with dichloromethane to give 2.37 g of the expected product.

Workup

  1. additionare added, at 20° C.
  2. concentrationthe reaction medium is concentrated
  3. washwashed twice with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-13414564263442c68aa76609a14d58c0
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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