[2-Chloro-6-(isopropylamino)phenyl]methanol → (2-Amino-6-chlorophenyl)methanol

HRID 2425759Notes

Reaction equation

HRID 2425759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][CH:9]([CH3:11])[CH3:10])[C:3]=1[CH2:12][OH:13]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:12][OH:13].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][CH:9]([CH3:11])[CH3:10])[C:3]=1[CH:12]=[O:13]

Participants

5

Reactant 1

HCID 59822478[2-Chloro-6-(isopropylamino)phenyl]methanol2×

Product 2

HCID 21925574(2-Amino-6-chlorophenyl)methanolHCID 598224892-Chloro-6-(isopropylamino)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of [2-chloro-6-(isopropylamino)phenyl]methanol, 5-chloro-2,2-dimethyl-1,4-dihydro-2H-3,1-benzoxazine (2.7 g, ratio; 1:1, step 2) and manganese dioxide (3.9 g, 33.8 mmol) in toluene (50 mL) was stirred at reflux temperature for 16 h. The mixture was filtrated through a pad of Celite and the filtrate was concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:30) to give 1.2 g (45% from (2-amino-6-chlorophenyl)methanol) of the title compound as a yellow solid.

Workup

  1. temperatureat reflux temperature for 16 h
  2. filtrationThe mixture was filtrated through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:30)

Sources & evidence

ORD record
ord-c3bc416f19b040758f177833d1c44064
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

Loading…