Ethanol → HCID 131721613, compound

HRID 850512Notes

Reaction equation

HRID 850512 reaction equation
[NH2:1][C:2]1[C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=O.[CH2:30](O)[CH3:31].C(CC(=O)C)(=O)C.C(OCC)(=O)C>Cl.[Cl-].[Na+].O>[CH3:29][O:28][C:20]1[CH:19]=[CH:18][C:3]2[C:2]([C:21]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[N:1][CH:30]([CH3:31])[N:6]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[CH:4]=2

Participants

7

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 31261AcetylacetoneHCID 19363465HCID 19363465, compound

Product 1

HCID 131721613HCID 131721613, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Amino-4-methoxy-N-[2-(4-nitrophenyl)ethyl]-3-pentyloxydenzamide (200 mg, 0.498 mmol) obtained in Example 2-46, ethanol (3 ml) and acetyl acetone (0.13 ml, 1.25 mmol) were mixed, and one drop of concentrated hydrochloric acid was added to this solution. The mixture was refluxed under heating for 2.5 hours, and ethyl acetate (30 ml) and saturated brine (30 ml) were added to separate the organic layer. This organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (20 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure to give a crude product of 7-methoxy-2-methyl-3-[2-(4-nitrophenyl)ethyl]-8-pentyloxy-3H quinazolin A one.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 2.5 hours
  3. customto separate the organic layer
  4. washThis organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ee2207a024154140a6a1f15bfdeda7a0
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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