Acetic Acid → HCID 54734744, compound

HRID 1658101Notes

Reaction equation

HRID 1658101 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7](O)=[O:8])[C:5]([NH:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.[C:14]([OH:17])(=O)[CH3:15]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]([CH2:12][CH3:13])[C:14](=[O:17])[CH:15]=[C:7]2[OH:8]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 1880316737494-82-9

Product 1

HCID 54734744HCID 54734744, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

5-Chloro-N-ethyl anthranilic acid (13.1g; 0.006 mole) in acetic acid (35 ml) and acetic anhydride (35 ml) was refluxed for 24 hours. The cooled mixture was poured into ice-water and basified to pH 14. The precipitated red oil was separated and the supernatant acidified to pH 5 to give the title compound as a white crystalline solid. m.p. (EtOH) 305°-8°C (Found C, 58.80; H, 4.64; N, 6.49; Cl, 15.95; C11H10CINO2 requires; C, 59.07; H, 4.51; N, 6.26; Cl, 15.85%).

Workup

  1. customThe precipitated red oil was separated

Sources & evidence

ORD record
ord-fb3b90041a4f453e859f3179c74d5d1b
Source dataset
uspto-grants-1976_06
Patent number
US03962445

Reaction notes

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