Methyl 4-aminobenzoate → HCID 58566937, compound

HRID 1676852Notes

Reaction equation

HRID 1676852 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+].[CH2:17]([O:24][CH2:25][C:26](Cl)=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:26](=[O:27])[CH2:25][O:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 58566937HCID 58566937, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-amino-benzoic acid methyl ester 11 (10 grams, 66.15 mmol) and sodium bicarbonate (11 grams, 131.67 mmol) in ethyl acetate (150 mL) at 0° C. is added benzyloxy acetyl chloride (16.6 grams, 89.93 mmol) drop wise. The reaction mixture is stirred at room temperature for 10 hours. The solids are filtered off. The ethyl acetate layer is washed with 5% sodium bicarbonate solution (2×25 mL), water (2×25 mL), dried over sodium sulfate, and distilled to get crude 12, which can be purified in a suitable solvent.

Workup

  1. filtrationThe solids are filtered off
  2. washThe ethyl acetate layer is washed with 5% sodium bicarbonate solution (2×25 mL), water (2×25 mL)
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled
  5. customto get crude 12, which
  6. customcan be purified in a suitable solvent

Sources & evidence

ORD record
ord-4c03c7e46cbd4c0eb456b22639b826fb
Source dataset
uspto-grants-2011_08
Patent number
US08007526B2

Reaction notes

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