Acetic Acid → 7-Chloro-4-hydroxy-1-methyl-2(1H)-quinolinone

HRID 1658102Notes

Reaction equation

HRID 1658102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:11][CH3:12])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[C:13](O)(=[O:15])[CH3:14]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6]([OH:8])=[CH:14][C:13](=[O:15])[N:11]2[CH3:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 125353684-Chloro-2-(methylamino)benzoic acid

Product 1

HCID 546962987-Chloro-4-hydroxy-1-methyl-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Refluxing a solution of 4-chloro-N-methyl anthranilic acid (13.6g; 0.073 mole) in acetic acid (37 ml) and acetic anhydride (37 ml) for 6 hours and work up as described in Example 35(a) gave the title compound; m.p. (AcOH, EtOH) 308°-9°. (Found; C, 56.97; H, 4.03; N, 6.89 Cl, 16.82; C10H8NClO 2 requires; C, 57.29; H, 3.85; N, 6.68; Cl, 16.91%).

Sources & evidence

ORD record
ord-022787c730bc49d783ecff68cc8e1cdd
Source dataset
uspto-grants-1976_06
Patent number
US03962445

Reaction notes

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