Acetic Acid → HCID 10731836, compound

HRID 472100Notes

Reaction equation

HRID 472100 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[OH-].[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(O)(=O)C>O>[CH2:18]([O:17][C:15]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 755984-Amino-3-methylbenzoic acid

Product 1

HCID 10731836HCID 10731836, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4-amino-3-methylbenzoic acid (35.1 g, 232 mmol) in water (400 mL) was treated with 2.5N NaOH (200 mL, 500 mmol) and benzyl chloroformate (37.0 mL, 259 mmol). After 1 h, 150 mL water was added, the resulting mixture was treated with glacial acetic acid (15 mL) and the solids collected by filtration. The filter cake was rinsed with water and the resulting solid taken up in ethyl acetate/2-methyl tetrahydrofuran. The organic was washed with brine, dried over MgSO4, filtered and concentrated. The resulting solid was dried under vacuum to give 45.1 g of the title compound. LCMS m/z=307.9 MH+, Rt=2.508 min.

Workup

  1. filtrationthe solids collected by filtration
  2. washThe filter cake was rinsed with water
  3. washThe organic was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-a1c9003ad8b345079e2a1b6e16d12676
Source dataset
uspto-grants-2014_01
Patent number
US08633206B2

Reaction notes

Loading…