2-Chloro-3-nitropyridine → 7-(3-Nitro-2-pyridinylamino)-1-(4-methyl-piperazinyl)-naphthalene

HRID 235126노트

반응식

HRID 235126 반응식
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.Cl[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1>CN(C)C1C=CN=CC=1.CN(C=O)C>[N+:26]([C:25]1[C:20]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)=[N:21][CH:22]=[CH:23][CH:24]=1)([O-:28])=[O:27]

참가 물질

5

반응물 2

HCID 796132-Chloro-3-nitropyridine2회HCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

생성물 1

HCID 189675077-(3-Nitro-2-pyridinylamino)-1-(4-methyl-piperazinyl)-naphthalene

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매2회HCID 6228Dimethylformamide용매2회

실험 절차

7-Amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.247 g, 1.02 mmol), 2-chloro-3-nitropyridine (0.325 g, 2.05 mmol), and 4-dimethylaminopyridine (0.062 g, 0.51 mmol) were combined in dry DMF (0.15 mL). The solution was refluxed 4 hours then 0.5 mL more DMF was added and the mixture was allowed to stir at ambient temperature overnight. 2-Chloro-3-nitropyridine (0.105 g, 0.69 mmol), and 4-dimethylaminopyridine (0.062 g, 0.51 mmol) were added and the mixture was refluxed 2 hours more. The solvent was removed in vacuo and the residue was taken up in methylene chloride. This organic phase was washed with 0.5N sodium hydroxide and brine; then it was dried over calcium sulfate and concentrated to a red oil which was flash chromatographed on silica gel (1×4 inches). Gradient elution with 50% to 75% ethyl acetate/hexane followed by elution with 100% ethyl acetate gave a dark colored oil which crystallized upon addition of ether (2 mL) to yield 0.19 g (51%) as a dark red solid: mp 127.5°-129° C. Analysis calculated for C20H21N5O2 ; C, 66.10; H, 5.82; N, 19.27. Found: C, 66.04; H, 5.81; N, 19.02.

후처리

  1. temperatureThe solution was refluxed 4 hours
  2. temperaturethe mixture was refluxed 2 hours more
  3. customThe solvent was removed in vacuo
  4. washThis organic phase was washed with 0.5N sodium hydroxide and brine
  5. dry with materialthen it was dried over calcium sulfate
  6. concentrationconcentrated to a red oil which
  7. customchromatographed on silica gel (1×4 inches)
  8. washGradient elution with 50% to 75% ethyl acetate/hexane
  9. washfollowed by elution with 100% ethyl acetate
  10. customgave a dark colored oil which
  11. customcrystallized upon addition of ether (2 mL)
  12. customto yield 0.19 g (51%) as a dark red solid

출처 및 근거

ORD 기록
ord-5e9c841e40774ef38bfd3430ce45146f
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597826

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