Hydrochloric Acid → HCID 23343022, compound

HRID 27474Notes

Reaction equation

HRID 27474 reaction equation
[C:1]([NH:5][C:6]1[CH:25]=[CH:24][C:9]2[C:10](=[O:23])[O:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)=[N:13][C:8]=2[CH:7]=1)(=[O:4])[CH2:2][CH3:3].CN(C)C=[O:29].O.Cl>C(N(CC)CC)C>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:12]([NH:13][C:8]2[CH:7]=[C:6]([NH:5][C:1](=[O:4])[CH2:2][CH3:3])[CH:25]=[CH:24][C:9]=2[C:10]([OH:11])=[O:23])=[O:29])=[CH:15][CH:16]=1)([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 130200727-(propionamido)-2-(4-carboxyphenyl)-4H-3,1-benzoxazine-4-one

Product 1

HCID 23343022HCID 23343022, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5 g of 7-(propionamido)-2-(4-carboxyphenyl)-4H-3,1-benzoxazine-4-one, 50 ml of dimethylformamide, 10 ml of water and 8 ml of triethylamine was heated at 80°-90° C. for a period of 10 hours. After being allowed to cool, the mixture was treated with dilute hydrochloric acid to adjust its pH between 2 and 3. The precipitating crystal was filtered, washed with water, and recrystallized from isopropyl alcohol to produce 4.1 g of 2-(4-carboxybenzamido)-4-propionamidobenzoic acid having a melting point in the range of 284° to 286° C. (decompose).

Workup

  1. temperaturewas heated at 80°-90° C. for a period of 10 hours
  2. temperatureto cool
  3. filtrationThe precipitating crystal was filtered
  4. washwashed with water
  5. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-e146d0062f9b4a5da8b3bcb25dfc3a18
Source dataset
uspto-grants-1980_09
Patent number
US04221814

Reaction notes

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