Anthranilic Acid → HCID 43823076, compound

HRID 2039522Notes

Reaction equation

HRID 2039522 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](Cl)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18].N1C=CC=CC=1>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 1049PyridineHCID 6452210Benzeneacetyl chloride, 4-nitro-

Product 1

HCID 43823076HCID 43823076, compoundYield 175.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (4-nitro-phenyl)-acetyl chloride (2.20 g, 11.05 mmol) in anhydrous dichloromethane (50 mL) was added 2-aminobenzoic acid (0.76 g, 5.50 mmol) followed by the addition of pyridine (3 mL). After stirring for 5 hours at rt, the cloudy solution was diluted with dichloromethane and thoroughly washed with 3 M HCl solution, then with brine and dried over Na2SO4. The solvent was removed and the solid crystallized from ethyl acetate to provide the title compound (2.9 g, 88% yield).

Workup

  1. washthoroughly washed with 3 M HCl solution
  2. dry with materialwith brine and dried over Na2SO4
  3. customThe solvent was removed
  4. customthe solid crystallized from ethyl acetate

Sources & evidence

ORD record
ord-eb0c92c5bef546cd8f5545742a6ccf70
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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