Water → 4(1H)-Quinolinone, 3-hydroxy-1-methyl-

HRID 358702Notes

Reaction equation

HRID 358702 reaction equation
C[O-].[Na+].C([O:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]([CH3:25])[CH:23]=O)=[O:15])(=O)C1C=CC=CC=1.O>ClCCl>[OH:12][C:13]1[C:14](=[O:15])[C:16]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:22]([CH3:23])[CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium Methoxide3×HCID 867446442-[2-(N-methylformamido)phenyl]-2-oxoethyl benzoate

Product 1

HCID 5900784(1H)-Quinolinone, 3-hydroxy-1-methyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium methoxide (17.75 g) was added to a stirred solution of 2-[2-(N-methylformamido) phenyl]-2-oxoethyl benzoate, obtained as described in Example 2a-d, (186 g) in dichloromethane (1300 ml) at 0° under nitrogen resulting in an exotherm to 25 to 30°. The mixture was recooled at 0° and a second portion of sodium methoxide (17.75 g) added resulting in a further exotherm and the resultant mixture stirred for 1 hour. Sodium methoxide (35.5 g) was then again added in two equal portions and the resultant mixture stirred at 0 to 10° for 1 hour. Water (1860 ml) was added over 70 minutes maintaining the temperature below 6°. The phases were separated and the dichloromethane phase was extracted with aqueous sodium hydroxide (0.5M, 930 ml). The combined aqueous phase and extract were washed with dichloromethane (930 ml) and then cooled to 0°. Hydrochloric acid ( 5M, 300 ml) was added dropwise to pH 3 to 4 followed by aqueous sodium hydroxide (5M, 38 ml) and then aqueous sodium bicarbonate (1M, 250 ml) to pH 8. The resultant solid was collected by filtration and washed with water (3×200 ml) to give 3-hydroxy-1-methyl-4-quinolone, m.p. 239°-241°.

Workup

  1. customobtained
  2. customwas recooled at 0°
  3. customresulting in a further exotherm
  4. temperaturemaintaining the temperature below 6°
  5. customThe phases were separated
  6. extractionthe dichloromethane phase was extracted with aqueous sodium hydroxide (0.5M, 930 ml)
  7. extractionThe combined aqueous phase and extract
  8. washwere washed with dichloromethane (930 ml)
  9. temperaturecooled to 0°
  10. additionHydrochloric acid ( 5M, 300 ml) was added dropwise to pH 3 to 4
  11. filtrationThe resultant solid was collected by filtration
  12. washwashed with water (3×200 ml)

Sources & evidence

ORD record
ord-389b62e649e44094ba0dfe46bf740607
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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