Isopropanol → HCID 18695390, compound

HRID 1870214Notes

Reaction equation

HRID 1870214 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.Cl.O1CCOCC1.[CH3:26][CH:27](O)[CH3:28]>>[F:1][C:2]1[CH:3]=[C:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH:27]([CH3:28])[CH3:26])=[O:17])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 18695414HCID 18695414, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 18695390HCID 18695390, compound

Procedure

A mixture of 2.19 g (8.55 mmol) of 5-(3-fluoro-6-nitrophenyl)aminovaleric acid, 100 ml of 2-propanol and 5 ml of 4N hydrochloric acid-dioxane was subjected to heating under reflux for 2 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (developing solvent: hexane:ethyl acetate=9:1 to 6:1) to give 2.55 g (stoichiometric) of isopropyl 5-(3-fluoro-6-nitrophenyl)aminovalerate.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column (developing solvent: hexane:ethyl acetate=9:1 to 6:1)

Sources & evidence

ORD record
ord-d1d83be968b847e4b5d1ef10d9051a14
Source dataset
uspto-grants-2000_08
Patent number
US06096743

Reaction notes

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