4-Chloroaniline → 1-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine hydrochloride

HRID 49859

반응식

HRID 49859 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C(O)CCC>[ClH:1].[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)=[CH:22][CH:21]=1

참가 물질

4

반응물 2

HCID 78124-ChloroanilineHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

생성물 1

HCID 98862921-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine hydrochloride

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of 1.28 g (5 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine, 0.67 g (5.25 mmol) 4-chloroaniline and 15 ml 1-butanol is heated for 0.5 h at 100 h while stirring in a nitrogen atmosphere. The mixture is then cooled to RT, filtered, and the filtrate washed with 1-butanol and ether. For purification, the crystallizate is dissolved in 40 ml of hot methanol, the solution treated with activated carbon, filtered via Hyflo Super Cel, and the filtrate evaporated to about half its original volume, resulting in the formation of a crystalline precipitate. After cooling to 0° C., filtration, washing of the filter residue with ether, and drying under HV for 8 h at 130° C., the title compound is obtained; m.p. >270° C.; 1H NMR (DMSO-d6) 9.80-11.40 (br), 8.89-8.94 (m, 1H), 8.67 (d, 2H), 8.25-8.30 (m, 1H), 8.06-8.17 (m, 2H), 7.87 (d, 2H), 7.69 (d, 2H), 7.49 (d, 2H), 4.81 (s, 2H); ESI-MS: (M+H)+=347.

후처리

  1. temperatureis heated for 0.5 h at 100 h
  2. filtrationfiltered
  3. washthe filtrate washed with 1-butanol and ether
  4. customFor purification
  5. dissolutionthe crystallizate is dissolved in 40 ml of hot methanol
  6. additionthe solution treated with activated carbon
  7. filtrationfiltered via Hyflo Super Cel
  8. customthe filtrate evaporated to about half its original volume
  9. customresulting in the formation of a crystalline precipitate
  10. temperatureAfter cooling to 0° C.
  11. filtrationfiltration
  12. washwashing of the filter residue with ether
  13. customdrying under HV for 8 h at 130° C.

출처 및 근거

ORD 기록
ord-a9a371c157ff4e519c612c2e0a5f8130
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710047B2

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