Sodium borohydride → 4-(4-(2-Methyl-2-aminopropyl)phenoxy)phenol

HRID 2119826Notes

Reaction equation

HRID 2119826 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([N+:21]([O-])=O)([CH3:20])[CH2:5][C:6]1[CH:19]=[CH:18][C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1.[BH4-].[Na+]>CO>[CH3:20][C:4]([NH2:21])([CH3:3])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 131723366Sodium borohydride 4-(4-(2-methyl-2-nitropropyl)phenoxy)phenol

Product 1

HCID 221477954-(4-(2-Methyl-2-aminopropyl)phenoxy)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of NiCl2.6H2O (1.40 g, 5.9 mmol) in MeOH (100 mL) was stirred at RT under a nitrogen atmosphere. Sodium borohydride (0.675 g, 17.9 mmol) was carefully added to the mixture in small portions. Twenty minutes after complete addition of the initial sodium borohydride 4-(4-(2-methyl-2-nitropropyl)phenoxy)phenol (3.20 g, 11 mmol) was added followed by the careful portionwise addition of more NaBH4 (1.58 g, 42 mmol) which caused a frothing exothermic reaction. All starting nitro compound had been consumed within 15 minutes of the last hydride addition as judged by TLC analysis. The mixture was then filtered through Celite and the filtrate concentrated in vacuo. The resulting residue was chromatographed over silica gel (MeOH/CHCl3) which allowed for isolation of both the incompletely reduced hydroxylamine product (0.675 g, 22%) and the desired amine product (0.94 g, 34%). MS (FD+): 258 (amine)

Workup

  1. additionwas added
  2. customa frothing exothermic reaction
  3. customAll starting nitro compound had been consumed within 15 minutes of the last hydride addition
  4. filtrationThe mixture was then filtered through Celite
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe resulting residue was chromatographed over silica gel (MeOH/CHCl3) which

Sources & evidence

ORD record
ord-e525799162da46c693e19b8563049239
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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