Tetrahydrofuran → HCID 19081868, compound

HRID 963364Notes

Reaction equation

HRID 963364 reaction equation
C([N-]C(C)C)(C)C.[Li+].[N:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=1.[Cl-:17].[NH4+:18].[C:19]([O:22][CH2:23][CH3:24])(=O)C.CC[CH2:27][CH2:28][CH2:29][CH3:30].C1C[O:34][CH2:33][CH2:32]1>>[NH2:18][C:29]1[C:28]([Cl:17])=[CH:27][C:24]([C:33](=[O:34])[CH2:32][CH:15]([OH:16])[C:12]2[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=2)=[C:23]([O:22][CH3:19])[CH:30]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 133894-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 21226206Ethyl acetate hexane

Product 1

HCID 19081868HCID 19081868, compound

Conditions

Temperature
0 °C

Procedure

4-Amino-5-chloro-2-methoxyacetophenone (12.75 g, 64 mmol), prepared as in Example 5, was suspended in THF (125 mL). The suspension was added to a -50° C. solution of lithium diisopropylamide (16.1 g, 150 mmol) in THF (200 mL) and the mixture was stirred at 0° C. for 15 minutes. Pyridine-4-carboxaldehyde (8.0 g, 75 mmol) was added and the mixture was allowed to warm to 5° C. Aqueous ammonium chloride was added and the mixture was extracted three times with ethyl acetate. The combined extracts were washed with water, dried over sodium sulfate, and concentrated in vacuo to leave a semi-solid residue. Ethyl acetate-hexane was added and filtration gave 1-(4-amino-5-chloro-2-methoxyphenyl)-3-hydroxy-3-(pyridin-4-yl)propan-1-one (12.1 g, 40 mmol), m.p. 181°-183° C.

Workup

  1. temperatureto warm to 5° C
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto leave a semi-solid residue
  7. filtrationfiltration

Sources & evidence

ORD record
ord-1e42f54cbd72456f871143dda58e17f4
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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