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Sodium borohydride → 6-Methyl-N4-(2-methylpropyl)-N2, N2-bis(phenylmethyl)pyridine-2,3,4-triamine

HRID 263719
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HRID 263719 반응식
[BH4-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]([N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([N+:25]([O-])=O)=[C:6]([NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:5]=1>CO.C(Cl)Cl.O.[Ni](Cl)Cl>[CH3:3][C:4]1[N:9]=[C:8]([N:10]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([NH2:25])=[C:6]([NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:5]=1
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참가 물질

6

반응물 2

HCID 4311764Sodium borohydride2회HCID 540930236-methyl-N4-(2-methylpropyl)-3-nitro-N2, N2-bis(phenylmethyl)pyridine-2,4-diamine

생성물 1

HCID 538812726-Methyl-N4-(2-methylpropyl)-N2, N2-bis(phenylmethyl)pyridine-2,3,4-triamine수율 85.1%

시약·촉매·용매 3

HCID 16212333Nickel chloride hydrate촉매HCID 887Methanol
용매
HCID 6344Dichloromethane용매

실험 절차

Sodium borohydride (585 mg, 16 mmole) was added to a solution of nickel (II) chloride hydrate (1.02 g, 4.3 mmole) in methanol (100 mL). The addition caused a black solid to form along with gas evolution. The resulting heterogeneous mixture was stirred at ambient temperature for 30 minutes. A solution containing 6-methyl-N4 -(2-methylpropyl)-3-nitro-N2, N2 -bis(phenylmethyl)pyridine-2,4-diamine (3.47 g, 8.6 mmole) in methylene chloride (20 mL) was added followed by the addition of sodium borohydride (1.37 g, 36 mmole). The reaction mixture was stirred at ambient temperature for about 30 minutes then eluted through a layer of silica gel with a methanol/methylene chloride mixture. The filtrate was concentrated under vacuum. The resulting residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried with magnesium sulfate and concentrated under vacuum to provide 2.74 g of the desired product as a green foam.

후처리

  1. additionThe addition
  2. customto form along with gas evolution
  3. additionwas added
  4. stirringThe reaction mixture was stirred at ambient temperature for about 30 minutes
  5. washthen eluted through a layer of silica gel with a methanol/methylene chloride mixture
  6. concentrationThe filtrate was concentrated under vacuum
  7. customThe resulting residue was partitioned between ethyl acetate and water
  8. customThe ethyl acetate layer was separated
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-42a2b14812b04f67bb95c1b179e2b081
출처 데이터셋
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05644063

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