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

HRID 241214Notes

Reaction equation

HRID 241214 reaction equation
Cl.Cl.[N+:3]([C:6]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]3[O:22][CH2:21][CH2:20][NH:19][CH2:18][C:17]=3[CH:23]=2)[CH:10]=[CH:9][C:7]=1[NH2:8])([O-:5])=[O:4].Cl[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[C:27]([CH3:35])[N:26]=1.C(N(C(C)C)CC)(C)C.O>CN1C(=O)CCC1>[CH3:35][C:27]1[N:26]=[C:25]([N:19]2[CH2:18][C:17]3[CH:23]=[C:13]([C:11]4[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:3]([O-:5])=[O:4])[CH:12]=4)[CH:14]=[CH:15][C:16]=3[O:22][CH2:21][CH2:20]2)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27854214-Chloro-2-methylquinazolineHCID 668203152-Nitro-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)aniline dihydrochloride

Product 1

HCID 668204944-[4-(2-Methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-2-nitroanilineYield 89%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-nitro-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)aniline dihydrochloride (323 mg, 1.0 mmol), 4-chloro-2-methylquinazoline (179 mg, 1.0 mmol), and diisopropylethylamine (700 uL, 4.0 mmol) in NMP (11 mL) was heated to 90° C. and stirred for 40 min. After cooling to rt, water was added to the reaction mixture. The orange precipitate formed was collected by filtration and then dried to provide 4-[4-(2-methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-2-nitroaniline (380 mg, 0.89 mmol, 89% yield) as a bright orange powder. MS (EI) for C24H21N5O3: 428 (MH+).

Workup

  1. customThe orange precipitate formed
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-ebf9dced85ba4251a30e3b0e0158070f
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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