Dimethyl aminoterephthalate → Methyl 2-amino-4-(hydroxymethyl)benzoate

HRID 1110100Notes

Reaction equation

HRID 1110100 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12](OC)=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Li+].[B-](CC)(CC)CC>C1COCC1>[NH2:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 79336Dimethyl aminoterephthalateHCID 23712863Lithium triethylborohydride

Product 1

HCID 602338Methyl 2-amino-4-(hydroxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-amino-4-carbomethoxybenzoate (12, 4.0 g, 19.0 mmol) was dissolved in dry THF and cooled in a dry ice-acetone bath under an inert atmosphere. Super-hydride (65 mL, 1.0M) was added slowly by syringe over a period of 1 h. A small aliquot of the solution was quenched with water and purified on a silica gel column to yield methyl 2-amino-4-hydroxymethylbenzoate as a white solid: mp. 100°- 102° C. 1H NMR (CDCl3) δ 3.82 (s, 3 H, CH3), 4.64 (s, 2 H, CH2), 5.82 (br s, 2 H, NH2), 6.58 (d, J=8.1 Hz, 1 H), 6.66 (br s, 1 H), 7.81 (d, J=8.0 Hz, 1 H); MS (CI/NH3) m/e 182 (MH+, base), 167, 150.

Workup

  1. temperaturecooled in a dry ice-acetone bath under an inert atmosphere
  2. customA small aliquot of the solution was quenched with water
  3. custompurified on a silica gel column

Sources & evidence

ORD record
ord-159abc1f23994588bf2266d56d386a62
Source dataset
uspto-grants-1994_06
Patent number
US05324832

Reaction notes

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