2-Amino-5-chlorobenzoic acid → HCID 379804, compound

HRID 1421882Notes

Reaction equation

HRID 1421882 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(O[C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(OCC)[CH2:16][CH3:17])C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Cl:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:16]([CH3:17])[C:4]2=[O:6]

Participants

4

Reactant 2

HCID 124762-Amino-5-chlorobenzoic acidHCID 12596498HCID 12596498, compound

Product 1

HCID 379804HCID 379804, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

To a mixture of 2-amino-5-chloro-benzoic acid (0.82 g, 4.80 mmol) in Dowtherm A (20 mL), was added the compound of Step A (1.0 g, 4.80 mmol). The mixture was warmed to reflux for 15 hours, then cooled to room temperature. Upon cooling, a white precipitate formed which was collected by filtration. The solid was triturated with diisopropyl ether followed by methylene chloride to give the title compound (0.58 g, 45%), m.p. 296-302° C. Anal. calcd. for C16H12CINO: C, 71.25; H, 4.48; N, 5.19. Found: C, 70.92; H, 4.44; N, 5.04.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 15 hours
  3. temperatureUpon cooling
  4. customa white precipitate formed which
  5. filtrationwas collected by filtration
  6. customThe solid was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-1499d30c045d4db7ba964c913af4b9b5
Source dataset
uspto-grants-2000_06
Patent number
US06080757

Reaction notes

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