4-Chloroaniline → HCID 178478209, compound

HRID 621592Notes

Reaction equation

HRID 621592 reaction equation
Cl[C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:3]=1.[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:3]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 787909Stk037974

Product 1

HCID 178478209HCID 178478209, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-4,5-dihydro-1-phenylpyrazole (1.8 g) and 4-chloroaniline (3.8 g) were fused under N2 at 140° for 20 minutes. The melt was cooled and the solid dissolved in CH2Cl2, washed with 1% HCl (×3), water, dried (Na2SO4), then absorbed into silica and column chromatographed using first 1:1 petrol: ether and then ether to give the title product as a yellow powder (1.0 g), (37%), m.p. 144°-7°.

Workup

  1. temperatureThe melt was cooled
  2. washwashed with 1% HCl (×3), water
  3. dry with materialdried (Na2SO4)
  4. customabsorbed into silica and column
  5. customchromatographed

Sources & evidence

ORD record
ord-f82f306ec9284ef595cef6afde22ce66
Source dataset
uspto-grants-1989_04
Patent number
US04824859

Reaction notes

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