3-Bromoaniline → (3-Bromophenyl)-[7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazolin-4-yl]-amine dihydrochloride

HRID 902433Notes

Reaction equation

HRID 902433 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([O:16][CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:13]([O:25][CH3:26])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Br:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31].[ClH:35].N1C=CC=CC=1>C(O)(C)C>[ClH:1].[ClH:35].[Br:27][C:28]1[CH:29]=[C:30]([NH:31][C:2]2[C:11]3[C:6](=[CH:7][C:8]4[CH:15]=[C:14]([O:16][CH2:17][CH2:18][N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)[C:13]([O:25][CH3:26])=[CH:12][C:9]=4[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 10176127Pyridinium chlorideHCID 250135374-Chloro-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazoline

Product 1

HCID 69269731(3-Bromophenyl)-[7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazolin-4-yl]-amine dihydrochlorideYield 84.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 0.1 g (0.267 mmol) of 4-chloro-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazoline in 3 mL of isopropanol is added 0.055 g (0.321 mmol) of 3-bromoaniline and 0.031 g (0.267 mmol) of pyridine hydrochloride. The mixture is brought to reflux for 15 minutes, then allowed to cool to room temperature. A yellow precipitate forms, which is filtered and washed with cold ethanol. Drying in vacuo provided 0.131 g of (3-bromophenyl)-[7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazolin-4-yl]-amine dihydrochloride as a yellow solid, mp 266-269° C.

Workup

  1. temperatureto reflux for 15 minutes
  2. filtrationA yellow precipitate forms, which is filtered
  3. washwashed with cold ethanol
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-3b097bf591484e21b00e85c6232002e7
Source dataset
uspto-grants-2008_04
Patent number
US07365197B2

Reaction notes

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