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Ammonium Acetate → [2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl ester

HRID 854580
Notes
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Reaction equation

HRID 854580 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6](=O)[CH:7]([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[N:13][CH:12]=1)[CH3:8])=[O:4].C([O-])(=O)C.[NH4+:24]>C(O)C>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]1[N:24]=[C:10]([C:11]2[CH:12]=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[O:9][C:7]=1[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 866045856-Chloro-nicotinic acid 3-methoxycarbonyl-1-methyl-2-oxo-propyl ester

Product 1

HCID 58765666[2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl esterYield 28.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-chloro-nicotinic acid 3-methoxycarbonyl-1-methyl-2-oxo-propyl ester (16.3 g, 57.1 mmol) and ammonium acetate (18.5 g, 240 mmol) in ethanol (150 mL) is heated at 80° C. for 2 h, concentrated. The residue is taken into acetic acid (330 mL) and heated to reflux overnight, concentrated. The residue is taken into ethyl acetate and washed with water, dried, concentrated, purified by column giving [2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-acetic acid methyl ester (4.3 g).

Workup

  1. concentrationconcentrated
  2. temperatureheated
  3. temperatureto reflux overnight
  4. concentrationconcentrated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. custompurified by column

Sources & evidence

ORD record
ord-5f10ed2fc9794b8e88d73155e565eba6
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259175B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes