Cyclohexene → HCID 53762858, compound

HRID 855683Notes

Reaction equation

HRID 855683 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:5][C:6]([N+:14]([O-])=O)=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].C1CCCCC=1>[Pd].CO.C(Cl)Cl>[NH2:14][C:6]1[CH:5]=[C:4]([O:17][CH2:18][CH2:19][O:20][CH3:21])[C:3]([O:2][CH3:1])=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 2

HCID 8079CyclohexeneHCID 21699291HCID 21699291, compound

Product 1

HCID 53762858HCID 53762858, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 5-methoxy-4-(2-methoxyethoxy)-2-nitrobenzoate (10.24 g, 34 mmol), cyclohexene (30 ml) and 10% palladium-on-charcoal catalyst (2.0 g) in methanol (150 ml) was heated at reflux for 5 hours. The reaction mixture was allowed to cool and diluted with methylene chloride. The catalyst was removed by filtration and the volatiles removed from the filtrate by evaporation. The residue was recrystallised from ethyl acetate/hexane to give ethyl 2-amino-5-methoxy-4-(2-methoxyethoxy)benzoate (8.0 g) as a buff solid. Formamide (80 ml) was added to this product and the mixture heated at 170° C. for 18 hours. About half the solvent was removed by evaporation under high vacuum and the residue was left to stand overnight. The solid product was collected by filtration, washed with ether and dried to give 6-methoxy-7-(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one (5.3 g, 62% over two steps) as a grey solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. temperatureto cool
  4. customThe catalyst was removed by filtration
  5. customthe volatiles removed from the filtrate by evaporation
  6. customThe residue was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e6ce45c48bb040d586a4526bf105f508
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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