Hydrochloric Acid → HCID 59590827, compound

HRID 2098973Notes

Reaction equation

HRID 2098973 reaction equation
[F:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9]([CH:12](C#N)[C:13]#N)([CH3:11])[CH2:8][CH2:7]2.[OH-:19].[K+].Cl.[OH2:22]>C(O)CO>[F:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9]([CH2:12][C:13]([OH:22])=[O:19])([CH3:11])[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 86648062HCID 86648062, compound

Product 1

HCID 59590827HCID 59590827, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
133 °C

Procedure

A solution of 38.3 (190 mg, 0.78 mmol) and potassium hydroxide (860 mg, 15 mmol) in water (0.5 mL) and ethylene glycol (1.0 mL) was heated in a sealed tube and stirred at 133° C. overnight. The reaction was cooled and then acidified with hydrochloric acid to pH ˜1. The mixture was extracted with EtOAc (5×), and the combined organic layers were dried over magnesium sulfate. The filtrate was concentrated to yield crude 38.4 and taken directly to the next step. MS ESI (neg.) m/e: 237.1 (M−H)−.

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe mixture was extracted with EtOAc (5×)
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationThe filtrate was concentrated
  5. customto yield crude 38.4

Sources & evidence

ORD record
ord-010295ddae5b48b1a42ed3430ff2da9c
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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