Hydrochloric Acid → 2-Acetyl-5-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-methyl-3-pyrazolidinone hydrochloride

HRID 1612949Notes

Reaction equation

HRID 1612949 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[N:19]([CH3:20])[NH:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:22].[C:23](OC(=O)C)(=[O:25])[CH3:24]>CCOCC>[ClH:22].[C:23]([N:18]1[C:17](=[O:21])[CH2:16][CH:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)[N:19]1[CH3:20])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 197927655-[3-(Cyclopentyloxy)-4-methoxyphenyl]-1-methyl-3-pyrazolidinone

Product 1

HCID 197927892-Acetyl-5-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-methyl-3-pyrazolidinone hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-[3-(Cyclopentyloxy)-4-methoxyphenyl]-1-methyl-3-pyrazolidinone (0.500 g) is dissolved in acetic anhydride (15 mL). The resulting solution is warmed to reflux for 2 hours, cooled to room temperature and concentrated in vacuo to afford an oil. This residue is dissolved in ether and treated with ethanolic HCl at room temperature. The resulting solid is stirred for 4 hours at room temperature, collected by suction and dried in vacuo to afford the title compound as a white powder (0.621 g; 98%) mp: 82°-85° C. 1H NMR (DMSO-d6, 400 MHz) δ6.88 (m, 3H); 3.85 (s, 3H); 2.82 (s, 3H); 2.52 (s, 3H); 2.00 (m, 2H); 1.84 (m, 3H); 1.64 (m, 2H). IR (KBr, cm-1) 1730.

Workup

  1. temperatureThe resulting solution is warmed
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated in vacuo
  4. customto afford an oil
  5. customcollected by suction
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ab47c019473347648edb80b5d9b6419b
Source dataset
uspto-grants-1993_03
Patent number
US05191084

Reaction notes

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