2,4-Dichloro-5-methoxyaniline → (2,4-Dichloro-5-methoxyphenyl)-[7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazolin-4-yl]-amine dihydrochloride

HRID 902432Notes

Reaction equation

HRID 902432 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.[Cl:27][C:28]1[CH:34]=[C:33]([Cl:35])[C:32]([O:36][CH3:37])=[CH:31][C:29]=1[NH2:30].Cl.N1C=CC=CC=1>C(O)(C)C>[ClH:1].[ClH:27].[Cl:27][C:28]1[CH:34]=[C:33]([Cl:35])[C:32]([O:36][CH3:37])=[CH:31][C:29]=1[NH:30][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[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[C:13]([O:25][CH3:26])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14766362,4-Dichloro-5-methoxyanilineHCID 10176127Pyridinium chlorideHCID 250135374-Chloro-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazoline

Product 1

HCID 69266630(2,4-Dichloro-5-methoxyphenyl)-[7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazolin-4-yl]-amine dihydrochlorideYield 61.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 0.05 g (0.133 mmol) of 4-chloro-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazoline in 2 mL of isopropanol is added 0.031 g (0.161 mmol) of 2,4-dichloro-5-methoxyaniline and 0.016 g (0.133 mmol) of pyridine hydrochloride. The mixture is brought to reflux for 2 hours, then allowed to cool to room temperature. A yellow precipitate formed, which is filtered and washed with cold isopropanol. Drying in vacuo provided 0.030 g of (2,4-dichloro-5-methoxyphenyl)-[7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinazolin-4-yl]-amine dihydrochloride as a yellow solid, mp 258-260° C.

Workup

  1. temperatureto reflux for 2 hours
  2. customA yellow precipitate formed
  3. filtrationwhich is filtered
  4. washwashed with cold isopropanol
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-b82083bcefae4958b0f65f193df65e21
Source dataset
uspto-grants-2008_04
Patent number
US07365197B2

Reaction notes

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