Hydrochloric Acid → HCID 67425350, compound

HRID 884335Notes

Reaction equation

HRID 884335 reaction equation
C[C:2](C)([O-:4])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[CH2:15][C:16]([CH2:18][NH:19][N:20]=[C:21](C)C(OCC)=O)=[O:17].Cl.[CH3:29]N(C=O)C>>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[C:15]1[C:2](=[O:4])[N:20]([CH3:21])[N:19]=[C:18]([CH3:29])[C:16]=1[OH:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 23665647Potassium tert-butoxideHCID 86643494HCID 86643494, compound

Product 1

HCID 67425350HCID 67425350, compound

Procedure

A solution of 2.1 g (2 eq) of potassium t-butoxide in 10 ml of DMF was initially charged, and 2.8 g (9.4 mmol) of ethyl 2-{[2-(2-chloro-6-fluorophenyl)acetyl]methylhydrazono}propionate in 10 ml of DMF was slowly added dropwise at <0° C. The mixture was allowed to warm to RT and then stirred for a further 0.5 hour. The reaction solution was then poured into 100 ml of cooled 1N hydrochloric acid and extracted twice with in each case 250 ml of ethyl acetate. The combined organic phases were washed with 50 ml of saturated sodium chloride solution and then dried with sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, ethyl acetate/n-heptane gradient). This gave 1.2 g of pure product.

Workup

  1. extractionextracted twice with in each case 250 ml of ethyl acetate
  2. washThe combined organic phases were washed with 50 ml of saturated sodium chloride solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography (silica gel, ethyl acetate/n-heptane gradient)

Sources & evidence

ORD record
ord-2c61d92043f3460cad1e04a81081ce38
Source dataset
uspto-grants-2012_08
Patent number
US08242055B2

Reaction notes

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