Triethylamine → HCID 70980047, compound

HRID 1749097Notes

Reaction equation

HRID 1749097 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25]>CCO>[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:23]=1[CH2:24][NH:25][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 70980047HCID 70980047, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cooled solution of 6-chloro-2-cyano-3-nitropyridine (52.0 g, 283 mmol) and triethylamine (43.0 mL, 425 mmol) in EtOH (950 mL) was added dropwise 2,4-dimethoxybenzylamine (53.2 mL, 312 mmol). The reaction was stirred at ambient temperature for 1.5 hours. The precipitate was filtered and washed with petrol to afford 75 g of 6-(2,4-dimethoxy-benzylamino)-3-nitro-pyridine-2-carbonitrile as a yellow solid. NMR 1H NMR (400 MHz, Me-d3-OD): 8.19 (1H, d), 7.24 (1H, d), 6.77 (1H, d), 6.57 (1H, d), 6.49 (1H, dd), 4.56 (2H, s), 3.86 (3H, s), 3.80 (3H, s). MS: [M+H]+=315.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with petrol

Sources & evidence

ORD record
ord-68b28be094574c9bb0478d135bb3833e
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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