Hydrochloric Acid → HCID 178524573, compound

HRID 2185198Notes

Reaction equation

HRID 2185198 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[C:12]([C:23]([O:25]C)=[O:24])[CH:13]=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[C:12]([C:23]([OH:25])=[O:24])[CH:13]=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=3)[N:10]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178498467HCID 178498467, compound

Product 1

HCID 178524573HCID 178524573, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(4-fluorophenyl)amino-4-hydroxy-6-nitroquinazoline-8-carboxylate (1.89 g) and lithium hydroxide monohydrate (5.182 g) in tetrahydrofuran (500 mL) and water (350 mL) was stirred at room temperature for 24 h. The reaction was acidified to pH 2 with 2 N hydrochloric acid, then was concentrated to ca. 400 mL. The yellow precipitate which formed was isolated by filtration, washed with water and dried to afford the title compound as a tan solid (1.16 g). 1H NMR (300 MHz, DMSO-d6 (w/TFA (50 uL)): 8.90 (d, J=2.6 Hz, 1H), 8.84 (d, J=2.6 Hz, 1H), 7.59 (dd, J=8.1, 4.9 Hz, 2H), 7.31 (t, J=8.8 Hz, 2H). HPLC (Method F): 5.97 min. MS (APCI+): m/z 345.

Workup

  1. concentrationwas concentrated to ca. 400 mL
  2. customThe yellow precipitate which formed
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-980b6645b8e448ab8420579e5468c4a5
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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