Acetic Acid → Methyl 3-(4-amino-3-cyclopentoxyphenyl)-E-propenoate hydrochloride

HRID 327601Notes

Reaction equation

HRID 327601 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[CH:10]=[CH:11][C:12]=2[N+:13]([O-])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[ClH:26]>CO.C(OCC)C.[Fe]>[ClH:26].[NH2:13][C:12]1[CH:11]=[CH:10][C:9](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])=[CH:8][C:7]=1[O:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 15052471Methyl 3-(3-cyclopentoxy-4-nitrophenyl)-E-propenoate

Product 1

HCID 70056690Methyl 3-(4-amino-3-cyclopentoxyphenyl)-E-propenoate hydrochloride

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2.1 g (7.2 mmol) of methyl 3-(3-cyclopentoxy-4-nitrophenyl)-E-propenoate in 30 mL of methanol was added 6.3 mL (110.1 mmol) of glacial acetic acid and 2.0 g (35.8 mmol) of iron filings. The mixture was warmed to reflux and stirred for 16 hours after which time it was cooled to room temperature, filtered over Celite 545, and concentrated. Liquid chromatography over 200 g of silica gel using 50% ethyl acetate in hexane provided a pure oil. The product was dissolved in anhydrous ethyl ether, subjected to a stream of anhydrous hydrogen chloride gas upon which time an analytically pure, hydrochloride solid formed. The desired solid was collected, washed several times with anhydrous ethyl ether, and dried in vacuo.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. filtrationfiltered over Celite 545
  4. concentrationconcentrated
  5. customLiquid chromatography over 200 g of silica gel using 50% ethyl acetate in hexane provided a pure oil
  6. customformed
  7. customThe desired solid was collected
  8. washwashed several times with anhydrous ethyl ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d9348e125ce049f9ad6fb7b970c21b4e
Source dataset
uspto-grants-1993_12
Patent number
US05274002

Reaction notes

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