Dimethyl acetylsuccinate → HCID 178499491, compound

HRID 472831

Reaction equation

HRID 472831 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([NH2:13])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:14]([CH:17]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:18](OC)=[O:19])(=O)[CH3:15]>CC1C=CC=CC=1C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]3[N:13]=[C:14]([CH3:15])[C:17]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[C:18]([OH:19])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 112039Dimethyl acetylsuccinateHCID 1785072813-(3-chlorophenyl)-1H-pyrazol-5-amine

Product 1

HCID 178499491HCID 178499491, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 7237O-XyleneSolvent

Procedure

To a solution of 3-(3-chlorophenyl)-1H-pyrazol-5-amine (23 g, 119 mmol), dimethyl 2-acetylsuccinate (22.35 g, 119 mmol) in o-Xylene (200 mL) was added p-toluenesulfonic acid monohydrate (100 mg, 0.526 mmol). The reaction mixture was heated at reflux under a Dean-Stark trap for 2 h. The solid was filtered and washed with hexanes to afford (39 g, 99%) of the title compound. 1H NMR (500 MHz, METHANOL-d4) δ 8.14-7.95 (m, 1H), 7.93-7.79 (m, 1H), 7.51-7.27 (m, 2H), 6.62-6.35 (m, 1H), 3.72 (s, 3H), 3.67 (s, 2H), 2.39 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a Dean-Stark trap for 2 h
  3. filtrationThe solid was filtered
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-c028003bb1d5422ca0439088bbb4d68e
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Linked notes

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