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

HRID 7629

Reaction equation

HRID 7629 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[C:9]([N+:16]([O-])=O)[CH:8]=1.FC1C=C(C=CC=1)COC(=O)[C:29]1C=CC(OCC2C=CC=C(F)C=2)=C[C:30]=1[N+:44]([O-])=O.COC(=O)C1C=CC(OCC2C=CC=C(F)C=2)=CC=1[N+:69]([O-])=O.O.[OH-].[Li+].[OH-].[Na+].[CH2:78]1[CH2:82][O:81]CC1>O>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:10]([C:11](=[O:13])[N:44]([CH2:78][C:82]([NH2:69])=[O:81])[C:30]([CH3:29])=[N:16]2)=[CH:14][CH:15]=1

Participants

8

Reactant 6

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 21991771HCID 21991771, compoundHCID 695943374-(3-Fluoro-benzyloxy)-2-nitro-benzoic acid methyl esterHCID 865936464-(3-Fluorobenzyloxy)-2-nitro-benzoic acid (3-fluoro-benzyl) ester

Product 1

HCID 100201802-[7-(3-Fluoro-benzyloxy)-2-methyl-4-oxo-4H-quinazolin-3-yl]-acetamideYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(3-Fluoro-benzyloxy)-2-nitro-benzoic acid: A mixture of 4-(3-fluorobenzyloxy)-2-nitro-benzoic acid (3-fluoro-benzyl) ester and 4-(3-fluoro-benzyloxy)-2-nitro-benzoic acid methyl ester (14.0 g, 35.0 mmol) in THF (120 mL) and water (120 mL), containing lithium hydroxide monohydrate (2.94 g, 70.1 mmol) was stirred at rt for 48 h. Then the mixture was poured into sodium hydroxide (2 N, 50 mL) and then the mixture extracted with diethyl ether (3×150 mL). The aqueous phase was then adjusted to pH 2 with HCl. Then the mixture was poured into sodium hydroxide (2 N, 50 mL) and the aqueous phase was then adjusted to pH 5.2 with HCl then the mixture extracted with diethyl ether (3×100 mL). The combined extracts were then washed with brine (100 mL) dried and evaporated to afford title compound (6.6 g, 65%) as a light yellow solid. MS: m/e=290.0 (M−H).

Workup

  1. extractionthe mixture extracted with diethyl ether (3×150 mL)
  2. additionThen the mixture was poured into sodium hydroxide (2 N, 50 mL)
  3. extractionthe mixture extracted with diethyl ether (3×100 mL)
  4. washThe combined extracts were then washed with brine (100 mL)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ad3689421b0444ecba177dceb56a6917
Source dataset
uspto-grants-2006_08
Patent number
US07087612B2

Linked notes

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