3-Chloro-4-(3-fluorobenzyloxy)aniline → 4-Quinazolinamine, N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-iodo-

HRID 571011Notes

Reaction equation

HRID 571011 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[NH2:17]>C(O)(C)C>[Cl:13][C:14]1[CH:15]=[C:16]([NH:17][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1

Participants

4

Reactant 2

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

Product 1

HCID 101745194-Quinazolinamine, N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-iodo-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-6-iodoquinazoline (5.7 g, 19.7 mmol) and 3-chloro-4-(3-fluorobenzyloxy)aniline (4.9 g, 19.7 mmol) was refluxed in isopropanol (150 mL) overnight. The mixture was cooled to room temperature. The solid product was precipitated, filtrated and dried in vacuum. The product 1405-174 was pure enough and used without further purification. (7.4 g, 74.2%): LC-MS: 506 [M+1]+, 1H NMR (DMSO-d6): δ 5.29 (s, 2 H), 7.18 (m, 1H), 7.33 (m, 3H), 7.48 (m, 1H), 7.66 (m, 1H), 7.74 (d, J=9.0 Hz, 1 H), 7.90 (d, J=2.2 Hz, 1 H), 8.37 (d, J=9.0 Hz, 1 H), 8.94 (s, 1 H), 9.29 (s, 1 H).

Workup

  1. customThe solid product was precipitated
  2. filtrationfiltrated
  3. customdried in vacuum
  4. customused without further purification

Sources & evidence

ORD record
ord-9d05e435b6e04eb2a6ce7bd9f05d5639
Source dataset
uspto-grants-2015_05
Patent number
US09024024B2

Reaction notes

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