Acetic Acid → 1-Ethyl-4-hydroxy-6-methylquinolin-2(1H)-one

HRID 1658098Notes

Reaction equation

HRID 1658098 reaction equation
[CH2:1]([NH:3][C:4]1[C:5](=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[C:6](O)=[O:7])[CH3:2].[C:14](OC(=O)C)(=O)[CH3:15].C(O)(=[O:23])C>>[CH2:14]([N:3]1[C:4]2[C:5](=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[C:6]([OH:7])=[CH:2][C:1]1=[O:23])[CH3:15]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 125113262-(Ethylamino)-5-methylbenzoic acid

Product 1

HCID 546963011-Ethyl-4-hydroxy-6-methylquinolin-2(1H)-one

Procedure

N-Ethyl-5-methyl anthranilic acid (17.6g- 0.098 mole, m.p. 159°C) was refluxed in acetic acid (43 ml) and acetic anhydride (43 ml) for 12 hrs. The dark red solution was cooled and poured onto crushed ice. The mixture was made alkaline filtered off tarry material and neutrallised with hydrochloric acid. The yellow crystalline product was filtered off, washed well with water and recrystallised from ethanol, m.p. 275°-280° (Found- C, 70,87, H, 6.34, N, 7.17 C12H13NO2 requires; C, 70.88; H, 6.44; N, 6.89%).

Workup

  1. temperatureThe dark red solution was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationfiltered off tarry material
  5. filtrationThe yellow crystalline product was filtered off
  6. washwashed well with water
  7. customrecrystallised from ethanol, m.p. 275°-280° (Found- C, 70,87, H, 6.34, N, 7.17 C12H13NO2 requires; C, 70.88; H, 6.44; N, 6.89%)

Sources & evidence

ORD record
ord-954e64d1eebe477199e25a899fb1b68d
Source dataset
uspto-grants-1976_06
Patent number
US03962445

Reaction notes

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