4-[4-(2-Methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-2-nitroaniline → 4-[4-(2-Methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]benzene-1,2-diamine

HRID 241215Notes

Reaction equation

HRID 241215 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:18][C:17]3[CH:19]=[C:20]([C:23]4[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([N+:30]([O-])=O)[CH:24]=4)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H][H]>C1COCC1.[Pd]>[CH3:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:18][C:17]3[CH:19]=[C:20]([C:23]4[CH:24]=[C:25]([NH2:30])[C:26]([NH2:27])=[CH:28][CH:29]=4)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 668204944-[4-(2-Methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 668203334-[4-(2-Methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]benzene-1,2-diamineYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(2-methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-2-nitroaniline (380 mg, 0.89 mmol) in THF (12 mL) was added palladium on carbon (wet, 100 mg). The resulting suspension was subjected to an atmosphere of hydrogen at 40 psi for 5 h. The catalyst was removed by filtration through celite, and the filtrate was concentrated to provide 4-[4-(2-methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]benzene-1,2-diamine (333 mg, 0.84 mmol, 94% yield) as a yellow-orange solid. MS (EI) for C24H23N5O: 398 (MH+).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b8c49481b3d54c06ade2b8bdf7df4e1b
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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