Hydrochloric Acid → HCID 21930398, compound

HRID 1178457Notes

Reaction equation

HRID 1178457 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6](F)[CH:5]=1.[OH:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([OH:22])[CH:21]=1)[CH:17]=[O:18].Cl>CN(C=O)C.O>[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([O:13][C:14]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:16]([CH:17]=[O:18])[CH:15]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 936554-Chloro-2-fluorobenzonitrileHCID 943653,5-Dihydroxybenzaldehyde

Product 1

HCID 21930398HCID 21930398, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (502 mg, 60% in mineral oil) was added portionwise to 4-chloro-2-fluorobenzonitrile (2.04 g) and 3,5-dihydroxybenzaldehyde (1.81 g) in DMF and the solution heated to 80° C. for 16 h. The cooled solution was diluted with water, acidified with concentrated hydrochloric acid, extracted twice with ethyl acetate, the extracts dried over sodium sulphate and evaporated. Purification by chromatography gave the sub-title compound as a white solid (0.83 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialthe extracts dried over sodium sulphate
  3. customevaporated
  4. customPurification by chromatography

Sources & evidence

ORD record
ord-3ca89c879b614c49bdfc03444c02313e
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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