Diazomethane → HCID 20096877, compound

HRID 1769604Notes

Reaction equation

HRID 1769604 reaction equation
[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:8]1=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[N+](=[CH2:26])=[N-]>ClCCl.C(O)C.CCOCC>[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH3:26])=[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:8]1=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 54679210HCID 54679210, compound

Product 1

HCID 20096877HCID 20096877, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.6 g of 1-hexyl-3-ethoxycarbonyl-4-hydroxy-2(1H)-quinolinone in dichloromethane (20 ml) and ethanol (2 ml) was treated with excess diazomethane in ether for 10 mins and is then evaporated. The crude methylation product upon chromatography on silica gel yielded 1-hexyl-3-ethoxycarbonyl-4-methoxy-2(1H)-quinolinone (1.0 g). This product (1 .0 g) in dry toluene (10 ml) was cooled to -78° C. and a 1M solution of diisobutyl aluminum hydride (4.3 ml) was added dropwise in 10min. After 2.5 hours stirring at-78° C. the reaction mixture was worked up by stirring with aqueous ammonium chloride/1N hydrochloric acid followed by extraction with methylene chloride. The crude reduction product was chromatographed on silica gel and crystallized from ethyl acetate/hexane to give 1-hexyl-3-formyl-4-methoxy-2(1H)-quinolinone as a crystalline solid. That the expected product was obtained was confirmed by the spectral data: MS (FAB): m/e 288 (M.+ +1); NMR (CDCl3): δ4.12 (s, 3H, OCH3), 10.5 (s, 1H, CHO).

Workup

  1. customis then evaporated

Sources & evidence

ORD record
ord-8c2cb6770b2b48e5921abe02aafec91f
Source dataset
uspto-grants-1995_01
Patent number
US05382572

Reaction notes

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