2-Methyl-2-butene → 6-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

HRID 1260953Notes

Reaction equation

HRID 1260953 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=[O:14])[N:9]([CH3:15])[C:8](=[O:16])[CH2:7][CH2:6]2.P([O-])(O)(O)=[O:18].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[C:13]([OH:18])=[O:14])[N:9]([CH3:15])[C:8](=[O:16])[CH2:7][CH2:6]2

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 101251786-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-7-carbaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 689356186-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acidYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixture of 6-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-7-carbaldehyde (2.0 g) synthesized by a known method (WO2001/077100), sodium dihydrogen phosphate (1.63 g) and 2-methyl-2-butene (4.3 ml) in tert-butanol (52 mL) and water (8 mL) was slowly added sodium chlorite (2.89 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. After cooling to 0° C., the reaction was quenched with 6N hydrochloric acid, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The obtained crystals were collected by filtration, and washed with hexane to give 6-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid (0.72 g, 34%) as white crystals.

Workup

  1. customat 0° C.
  2. temperatureAfter cooling to 0° C.
  3. customthe reaction was quenched with 6N hydrochloric acid
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. filtrationThe obtained crystals were collected by filtration
  9. washwashed with hexane

Sources & evidence

ORD record
ord-8abaf4272987482d803f8f4bc7ee4b48
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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