Water → HCID 59549185, compound

HRID 1096478Notes

Reaction equation

HRID 1096478 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=1.N1C=CC=CC=1.O>C1COCC1.C(OCC)(=O)C>[CH3:18][C:14]1[N:13]=[C:12]([NH:11][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 157652-Amino-6-methylpyridineHCID 15891Phenyl chloroformate

Product 1

HCID 59549185HCID 59549185, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenyl chloroformate (232 mL, 1.84 mol) was added dropwise (1.5 h) to a cooled (0° C.) solution of 2-amino-6-picoline (200 g, 1.84 mol) and pyridine (448 mL, 5.55 mol) in THF (1.6 L). The reaction was stirred, with continued cooling for 15 h. Water (500 mL) was added slowly (30 min) and then the mixture was diluted with ethyl acetate (2 L). The layers were separated and the organic layer was washed with 1 N hydrochloric acid (3×1 L), 1 N aqueous sodium hydroxide solution (500 mL) and brine (500 mL). The organic layer was then dried over sodium sulfate and concentrated under reduced pressure. The residue was suspended in hexane (500 mL) for 30 min and then filtered to afford the desired product (220 g, 52%) containing some trace impurities. 1H-NMR (300 MHz, DMSO-d6) δ 10.68 (s, 1H), 6.93-7.74 (m, 8H), 2.42 (s, 3H); ES-MS m/z 229.4 (MH)+; HPLC RT (Method A) 2.94 min.

Workup

  1. temperaturewith continued cooling for 15 h
  2. customThe layers were separated
  3. washthe organic layer was washed with 1 N hydrochloric acid (3×1 L), 1 N aqueous sodium hydroxide solution (500 mL) and brine (500 mL)
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationfiltered

Sources & evidence

ORD record
ord-cd1f1bb6db9249aea5c270bac520731a
Source dataset
uspto-grants-2012_03
Patent number
US08138336B2

Reaction notes

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