Methyl 4-Amino-3-chlorobenzoate → (4-Amino-3-chlorophenyl)methanol

HRID 630389Notes

Reaction equation

HRID 630389 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[Cl:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].NC1C(Cl)=CC(CO)=C(OC)C=1>O1CCCC1>[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[Cl:12]

Participants

5

Reactant 3

HCID 1515284Methyl 4-Amino-3-chlorobenzoateHCID 21226445Aluminium lithium hydrideHCID 55277042(4-Amino-5-chloro-2-methoxyphenyl)methanol

Product 1

HCID 13843958(4-Amino-3-chlorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Obtained as a light brown solid (76%) starting from commercially available methyl 4-amino-3-chlorobenzoate (4 g; 0.021 mol) and lithium aluminium hydride (1.09 g; 0.028 mol) in 144 ml tetrahydrofuran following the experimental procedure as described for intermediate 38.

Sources & evidence

ORD record
ord-3ac020c2dd284d98b86967f778435863
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

Loading…