Benzoic acid, 2-amino-3-chloro-, methyl ester → (2-Amino-3-chlorophenyl)methanol

HRID 1985532Notes

Reaction equation

HRID 1985532 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 11030511Benzoic acid, 2-amino-3-chloro-, methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 14155407(2-Amino-3-chlorophenyl)methanolYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-amino-3-chlorobenzoate (1.7 g, 9.16 mmol) in THF (40 mL) was dropwise added to a suspension of the LAH (521 mg, 13.7 mmol) in THF (15 mL) at room temperature over 10 min under N2, and stirred for 2 hrs. The reaction was carefully quenched with saturated Na2SO4 (10 mL) at 0° C., extracted with Et2O (2×50 mL). The combined organic layers were washes with brine (30 mL), dried on MgSO4, and concentrated on rotary vacuum to afford the expected product as a yellow solid (1.08 g, 75%), which was pure enough to be used in the next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 1.65 (s, 1H), 4.59-4.70 (m, 4H), 6.60-6.65 (m, 1H), 6.96 (dd, J=7.55, 1.26 Hz, 1H), 7.19-7.25 (m, 1H); Mass spec. 158.02 (MH+), Calc. for C7H8ClNO2 157.03.

Workup

  1. customThe reaction was carefully quenched with saturated Na2SO4 (10 mL) at 0° C.
  2. extractionextracted with Et2O (2×50 mL)
  3. customdried on MgSO4
  4. concentrationconcentrated on rotary vacuum

Sources & evidence

ORD record
ord-509745c59192416d87415d11a7cf2b1b
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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