5-Amino-2-chloro-4-fluorophenol → HCID 22624880, compound

HRID 1420946Notes

Reaction equation

HRID 1420946 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH2:28])=[C:26]([F:32])[CH:25]=1>C(O)(C)C>[ClH:20].[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:28][C:27]3[CH:29]=[C:30]([OH:31])[C:24]([Cl:23])=[CH:25][C:26]=3[F:32])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 220308367-(Benzyloxy)-4-chloro-6-methoxyquinazoline hydrochloride

Product 1

HCID 22624880HCID 22624880, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (169 mg, 0.5 mmol), (prepared as described for the starting material in Example 1), and 4-chloro-2-fluoro-5-hydroxyaniline (97 mg, 0.6 mmol), (EP 061741 A2), in isopropanol (5 ml) was heated at reflux for 2 hours. The resulting precipitate was collected by filtration, washed with isopropanol and ether and dried under vacuum to give 7-benzyloxy4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxyquinazoline hydrochloride (197 mg, 85%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with isopropanol and ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ff43fa3828b843638f95dc2fda557439
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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