3-Chloro-4-(3-fluorobenzyloxy)aniline → [3-Chloro-4-(3-fluorobenzyloxy)phenyl](6-iodoquinazolin-4-yl)amine hydrochloride

HRID 877079Notes

Reaction equation

HRID 877079 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=2)[N:22]=[CH:21][N:20]=1>C(O)(C)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

4

Reactant 2

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 66623345[3-Chloro-4-(3-fluorobenzyloxy)phenyl](6-iodoquinazolin-4-yl)amine hydrochlorideYield 116.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Chloro-4-(3-fluoro-benzyloxy)-phenylamine (3.1 g, 12 mmol) and 4-chloro-6-iodo-quinazoline (3.28 g, 11.3 mmol) were dissolved in isopropanol (50 ml). The reaction mixture was refluxed for 12 hours. The solid product was collected by filtration, washed with cold isopropanol (10 mL) and ether (20 mL), and air dried to afford 3.8 g of the clean desired material.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. filtrationThe solid product was collected by filtration
  3. washwashed with cold isopropanol (10 mL) and ether (20 mL), and air
  4. customdried

Sources & evidence

ORD record
ord-260505efcccc435a95f1382a3c1cbb0e
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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