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

HRID 263719
ノート
印刷プレビュー

反応式

HRID 263719 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 4311764Sodium borohydride2 回HCID 540930236-methyl-N4-(2-methylpropyl)-3-nitro-N2, N2-bis(phenylmethyl)pyridine-2,4-diamine

生成物 1

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

試薬・触媒・溶媒 3

HCID 16212333Nickel chloride hydrate触媒HCID 887Methanol
溶媒
HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-42a2b14812b04f67bb95c1b179e2b081
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05644063

反応ノート

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