Ammonium Acetate → HCID 86720535, compound

HRID 1755247Notes

Reaction equation

HRID 1755247 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH:16]=O)[CH:3]=1.C([O-])(=O)C.[NH4+:22]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:14][CH:15]=1)[N:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:22]=[CH:16]2

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 86720536HCID 86720536, compound

Product 1

HCID 86720535HCID 86720535, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of ethyl 2-(4-chloro-2-formyl-anilino)-2-oxo-acetate (0.14 g, 0.55 mmol, 1 eq) in 5.5 mL of acetic acid was added ammonium acetate (0.42 g, 5.4 mmol, 10 eq). After heating at 115° C. for 1 h, the mixture was concentrated then diluted with H2O and extracted with ethyl acetate. The organic layer was concentrated and the residue was purified on silica gel column chromatography (hex:EtoAc 3:2) to give ethyl 6-chloroquinazoline-2-carboxylate (0.11 g, 0.48 mmol, 88%).

Workup

  1. concentrationthe mixture was concentrated
  2. additionthen diluted with H2O
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified on silica gel column chromatography (hex:EtoAc 3:2)

Sources & evidence

ORD record
ord-5d885d1b404e43d5b0e4ecacdb1e62ef
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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