Water → HCID 21704199, compound

HRID 1595197Notes

Reaction equation

HRID 1595197 reaction equation
Cl.[NH2:2][CH:3]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1OC)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[C:20](OC(=O)C)(=[O:22])C.[OH2:27].N1[CH:33]=[CH:32]C=CC=1>>[C:32]([NH:2][CH:3]([C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([O:22][CH3:20])[CH:11]=1)=[O:5])(=[O:27])[CH3:33]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67551529HCID 67551529, compound

Product 1

HCID 21704199HCID 21704199, compound

Procedure

To a solution of 2-amino-3-methoxy-2-(4-pyridyl)acetophenone hydrochloride (0.5 g, 1.8 mmol) in pyridine (8 mL) was added acetic anhydride (1 mL). The mixture was stirred at rt for 45 min, then poured into H2O. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with sat'd NaCl, then dried over MgSO4. Evaporation of solvent gave a red oil which was purified by flash chromatography, eluting with a solvent gradient of 0-4% MeOH/CHCl3. The title compound was isolated as a yellow oil (0.21 g).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. washThe combined organic layers were washed with sat'd NaCl
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent
  6. customgave a red oil which
  7. customwas purified by flash chromatography
  8. washeluting with a solvent gradient of 0-4% MeOH/CHCl3

Sources & evidence

ORD record
ord-0c0466f669f24519a68faf3c4012a25b
Source dataset
uspto-grants-2001_09
Patent number
US06288062B1

Reaction notes

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