Ethyl Acetate → HCID 178419928, compound

HRID 2264209Notes

Reaction equation

HRID 2264209 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH2:18])=[C:8]([NH2:19])[N:7]=1.[CH2:20](OC(OCC)OCC)C.[OH-].[Na+].C(OCC)(=O)C>C(O)(=O)C>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:7]=[C:8]2[NH:19][CH:20]=[N:18][C:9]2=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 31214Ethyl orthoformateHCID 59595986HCID 59595986, compound2×

Product 1

HCID 178419928HCID 178419928, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-(1,3-oxazol-2-yl)-3,4′-bipyridine-5,6-diamine (Intermediate 10, 0.100 g, 0.39 mmol) and triethylorthoformate (0.117 g, 0.79 mmol) in glacial acetic acid (2 mL) was heated in a sealed tube to 140° C. After stirring for 2 hours, the mixture was cooled and taken to pH 7 with 6N aqueous sodium hydroxide solution. Ethyl acetate was added to the mixture and, after stirring for 30 minutes, the separated solid was filtered, washed with diethyl ether and dried in vacuo to give the title compound (0.047 g, 49%) as an off-white solid.

Workup

  1. temperaturethe mixture was cooled
  2. stirringafter stirring for 30 minutes
  3. filtrationthe separated solid was filtered
  4. washwashed with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-575934924e984483af34fa8dd6ef9788
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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