Diisopropylethylamine → HCID 178490961, compound

HRID 537023Notes

Reaction equation

HRID 537023 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][N+:3]=1[O-:12].[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[CH2:23][NH2:24].CCN(C(C)C)C(C)C>C(O)CCC>[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[CH2:23][NH:24][C:2]1[N+:3]([O-:12])=[CH:4][C:5]([CH3:11])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5972502,4-DimethoxybenzylamineHCID 123180102-Chloro-5-methyl-4-nitropyridine N-oxide

Product 1

HCID 178490961HCID 178490961, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-chloro-5-methyl-4-nitropyridine 1-oxide (1.1 g, 5.8 mmol), 1-(2,4-dimethoxyphenyl)methanamine (1.1 mL, 7.0 mmol), DIEA (2.0 mL, 11.6 mmol), and 1-butanol (9 mL) was subjected to microwave irradiation at 120° C. for 8 h. The reaction mixture was allowed to cool to rt and was filtered. The resulting solid was washed with water (20 mL) and dried to give N-(2,4-dimethoxybenzyl)-5-methyl-4-nitropyridin-2-amine 1-oxide (1.2 g, 67%), which was used in the next step without further purification.

Workup

  1. customirradiation at 120° C. for 8 h
  2. filtrationwas filtered
  3. washThe resulting solid was washed with water (20 mL)
  4. customdried

Sources & evidence

ORD record
ord-7a5cd65f1f8f4442ace8f43d5294dc96
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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