HCID 15703646, compound → HCID 15703647, compound

HRID 2351280Notes

Reaction equation

HRID 2351280 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[CH2:17])[C:8]=1[C:9]([OH:11])=[O:10])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH3:17])[C:8]=1[C:9]([OH:11])=[O:10])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 15703646HCID 15703646, compound

Product 1

HCID 15703647HCID 15703647, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Ethoxycarbonylamino-6-vinyl benzoic acid (500 mg, 2.13 mmol) and 10% Pd-C (50 mg) in 40 ml absolute ethanol was stirred for 16 hrs under 40 psi H2 pressure in a Parr bomb at room temperature. The reaction mixture was filtered through a cone of Celite and the catalyst on Celite was washed with 15 ml ethanol. The combined filtrate was evaporated to dryness. Trituration with ether gave crystalline 2-ethoxycarbonylamino-6-ethylbenzoic acid of Formula (I) in quantitative yield. M.p. 71.5°-74.0° C.; IR (KBr) νmax =1725, 1700 cm-1. Analysis, C12H15NO4 : theory, C 60.75; H 6.37; H 5.90; found, C 60.82; H 6.38; N 5.88.

Workup

  1. filtrationThe reaction mixture was filtered through a cone of Celite
  2. washthe catalyst on Celite was washed with 15 ml ethanol
  3. customThe combined filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ef8e11e57e5645dcbf54c836ef87cb83
Source dataset
uspto-grants-1989_10
Patent number
US04873232

Reaction notes

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