Phenyl 4-aminosalicylate → HCID 12083215, compound

HRID 1359536Notes

Reaction equation

HRID 1359536 reaction equation
[C:1]1([O:7][C:8](=[O:17])[C:9]2[C:10](=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OC(=O)C)(=O)C>[C:1]1([O:7][C:8](=[O:17])[C:9]2[CH:15]=[CH:14][C:13]([NH:16][C:1](=[O:7])[CH3:2])=[CH:12][C:10]=2[O:11][C:10](=[O:11])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 8609Phenyl 4-aminosalicylate

Product 1

HCID 12083215HCID 12083215, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

This compound was prepared using the General Structural Outline for Synthesis of para-Aminosalicylic Acid Phenyl Ester Diacyl Derivatives. In a 50 mL pear shaped flask fitted for reflux were mixed para-aminosalicylic acid phenyl ester (1.45 g) and acetic anhydride (10 mL). Over 10 minutes, the mixture was brought to the boil, and refluxing was continued for 20 minutes. The mixture was allowed to cool to room temperature and stand for two hours, then poured out into a watchglass and allowed to dry. The resulting residue was ground with ether (10 mL) and the process repeated. The resulting white crystalline solid was the title compound (0.75 g, 38%), mp 142-143° C. (uncorr); IR v 3323, 1767, 1734, 1673, 1613, 1590, 1506, 1268, 1207, 1185, 1163, 1134, 1056, 1014, 1002, 944, 895, 862, 844, 748, 691 cm−1; NMR δ 10.5 (1H, br s), 8.2-7.1 (m, 8H), 2.2 (3H, s), 2.1 (3H, s).

Workup

  1. customThis compound was prepared
  2. customIn a 50 mL pear shaped flask fitted
  3. temperaturefor reflux
  4. temperaturerefluxing
  5. waitwas continued for 20 minutes
  6. waitstand for two hours
  7. additionpoured out into a watchglass
  8. customto dry

Sources & evidence

ORD record
ord-94426b01043a49d38828a4cb1ea9a51a
Source dataset
uspto-grants-2003_07
Patent number
US06600063B1

Reaction notes

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