Potassium Carbonate → [2-Chloro-6-(isopropylamino)phenyl]methanol

HRID 2425758Notes

Reaction equation

HRID 2425758 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][OH:10].O.[C:12]([O-])(=O)[CH3:13].[Na+].[BH4-].[Na+].[C:19](=O)([O-])[O-].[K+].[K+]>[OH-].[Na+].O.C(O)C.CC(C)=O.C(O)(=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH:12]([CH3:13])[CH3:19])[C:3]=1[CH2:9][OH:10]

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 21925574(2-Amino-6-chlorophenyl)methanolHCID 23681166Acetic acid, sodium salt, monohydrate

Product 1

HCID 59822478[2-Chloro-6-(isopropylamino)phenyl]methanolYield 94%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of (2-amino-6-chlorophenyl)methanol (2.3 g, 14.6 mmol, step 1), acetic acid (14 mL), sodium acetate hydrate (4.8 g, 58.5 mmol), acetone (7 mL), ethanol (4.8 mL), and water (14 mL) was added a solution of sodium borohydride (1.66 g, 43.9 mmol) in 2N aqueous sodium hydroxide solution (4.8 mL) at 0° C. over a period of 4 h. The mixture was basified with potassium carbonate (3 g) and added water (150 mL). The aqueous layer was extracted with n-hexane. The organic layer was dried over sodium sulfate and concentrated in vacuo to give 2.74 g of the mixture of title compound and 5-chloro-2,2-dimethyl-1,4-dihydro-2H-3,1-benzoxazine (1:1). The mixture was used next reaction without further purification.

Workup

  1. extractionThe aqueous layer was extracted with n-hexane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9ec01adefc2410d83bff7d49056df9b
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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