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Hydrochloric Acid → 2-[7-(3-Fluoro-benzyloxy)-4-oxo-4H-quinazolin-3-yl]-acetamide

HRID 7626
Notes
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Reaction equation

HRID 7626 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:17])[NH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1.[Na].FC1C=C(C=CC=1)CO.FC1C=C2[C:35]([C:36](=[O:42])[NH:37]C=N2)=CC=1.Cl>O>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:17])[N:12]([CH2:35][C:36]([NH2:37])=[O:42])[CH:13]=[N:14]2)=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 680083-Fluorobenzylic alcoholHCID 5360545SodiumHCID 1353984967-Fluoroquinazolin-4(3H)-oneHCID 1357527167-(3-Fluoro-benzyloxy)-3H-quinazolin-4-one

Product 1

HCID 98621802-[7-(3-Fluoro-benzyloxy)-4-oxo-4H-quinazolin-3-yl]-acetamide
Yield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-(3-Fluoro-benzyloxy)-3H-quinazolin-4-one: Sodium (1.8 g, 78.6 mmol) was added portionwise to 3-fluorobenzyl alcohol and the resulting mixture heated at 80–90° C. for 4 h under Argon. The resulting suspension was cooled to rt and 7-fluoro-3H-quinazolin-4-one (3.2 g, 19.5 mmol) was added and the resulting mixture heated at 130–140° C. for 14 h. The solid formed was then dissolved with water (400 mL) and the mixture acidified to pH 3–4 with HCl (4 N). The resulting precipitate was then filtered off, washed with water (100 mL) and diethylether (100 mL). Recrystallisation from tetrahydrofuran: ethylacetate (1:1) afforded the title compound (3.2 g, 61%) as white crystals. MS: m/e=271.3 (M+H+).

Workup

  1. temperaturethe resulting mixture heated at 80–90° C. for 4 h under Argon
  2. temperaturethe resulting mixture heated at 130–140° C. for 14 h
  3. customThe solid formed
  4. filtrationThe resulting precipitate was then filtered off
  5. washwashed with water (100 mL) and diethylether (100 mL)
  6. customRecrystallisation from tetrahydrofuran: ethylacetate (1:1)

Sources & evidence

ORD record
ord-af083bdcb1c9493f8949656570ce9951
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087612B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes