Acetic Acid → HCID 178470310, compound

HRID 625804Notes

Reaction equation

HRID 625804 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[NH:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:3])[NH2:2].CC(C)([O-])C.[K+].[Na+].[Cl-].CC(O)=O>CCO>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]2[C:5]=1[N:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:2]=[C:1]2[OH:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 23665647Potassium tert-butoxideHCID 66610273Ethyl 2-(2-carbamoyl-6-fluorophenylamino)-2-oxoacetate

Product 1

HCID 178470310HCID 178470310, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(2-carbamoyl-6-fluorophenylamino)-2-oxoacetate (600 mg, 2.4 mmol) and potassium t-butoxide (300 mg, 6.7 mmol) in EtOH (10 mL) was stirred at rt for 5 h. Saturated aq NaCl (50 mL) and HOAc (0.5 mL) were added and the mixture was extracted with EtOAc (3×80 mL). The combined organic layers were washed with brine (80 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford ethyl 8-fluoro-4-hydroxyquinazoline-2-carboxylate (530 mg, 93%). 1H NMR (300 MHz, DMSO-d6) δ 1.39 (t, J=7.2 Hz, 3H), 4.40 (q, J=7.2 Hz, 2H), 7.57-7.70 (m, 1H), 7.78 (t, J=9.2 Hz, 1H), 7.99 (d, J=8.1 Hz, 1H), 12.86 (s, 1H); LC-MS (ESI) m/z 237 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×80 mL)
  2. washThe combined organic layers were washed with brine (80 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3eda936244c4f14995a0704353862f4
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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