1-tert-Butoxy-N,N,N',N'-tetrapropylmethanediamine → N,N-dipropyl-N-[2-(7-nitro-1H-indazol-4-yl)ethenyl]amine

HRID 1032525

Reaction equation

HRID 1032525 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.C(O[CH:19](N(CCC)CCC)[N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])(C)(C)C>O1CCCC1>[CH2:21]([N:20]([CH2:24][CH2:25][CH3:26])[CH:19]=[CH:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2)[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 137713131-tert-Butoxy-N,N,N',N'-tetrapropylmethanediamineHCID 221660184-Methyl-7-nitro-1H-indazole

Product 1

HCID 54102292N,N-dipropyl-N-[2-(7-nitro-1H-indazol-4-yl)ethenyl]amineYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.1 g of 4-methyl-7-nitro-1H-indazole and 5.0 g of tert-butoxybis(dipropylamino)methane are heated to 80° C. in 10 ml of tetrahydrofuran for 2.5 hours. The mixture is concentrated, distilled with tetrahydrofuran, and recrystallized from dichloromethane/hexane, yielding 3.1 g of N,N-dipropyl-N-[2-(7-nitro-1H-indazol-4-yl)ethenyl]amine, mp 166°-167° C.

Workup

  1. concentrationThe mixture is concentrated
  2. distillationdistilled with tetrahydrofuran
  3. customrecrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-76073e69a49c4844a03b0e57a7e14f84
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Linked notes

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