Water → 1-(3-amino-benzyl)-4-(4-isopropyl-phenyl)-6-propargyloxy-1H-quinazolin-2-one

HRID 445174Notes

Reaction equation

HRID 445174 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][C:22]#[CH:23])[CH:18]=3)[N:13]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-])=O)[CH:26]=3)[C:12](=[O:34])[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(OCC)(=O)C.O>C(O)(=O)C.[Fe]>[NH2:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][N:13]1[C:14]2[C:19](=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[CH:16][CH:15]=2)[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5][CH:6]=2)=[N:11][C:12]1=[O:34]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 451416224-(4-isopropyl-phenyl)-1-(3-nitro-benzyl)-6-propargyloxy-1H-quinazolin-2-one

Product 1

HCID 451416231-(3-amino-benzyl)-4-(4-isopropyl-phenyl)-6-propargyloxy-1H-quinazolin-2-oneYield 110.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5.7 g (12.57 mmol) of the aromatic nitro-compound prepared in step B and 5.7 g (0.10 mol; 8 eq.) iron powder in 85 ml acetic acid is heated to 40° C. and stirred overnight. After 16 h another 3.5 g iron powder is added and stirring continued for 4 h. The brown suspension is distributed between ethyl acetate and water. The organic layer is washed with sodium bicarbonate solution and brine. Concentration in vacuo leaves 5.88 g of yellow foam. Flash chromatography (petroleum ether/ethyl acetate) yields 2.80 g (53%) of a yellow solid. m.p. 186° C.

Workup

  1. stirringstirring
  2. waitcontinued for 4 h
  3. washThe organic layer is washed with sodium bicarbonate solution and brine
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-3b1dce04206c440d8bd2c5f160ab0118
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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