Acetic Acid → HCID 71610559, compound

HRID 1399802Notes

Reaction equation

HRID 1399802 reaction equation
[Cl:1][C:2]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:7]=1.[CH3:26][C:27](O)=O>[Fe]>[Cl:1][C:2]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:6]2=[N:7][C:8]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:10]=[C:11]2[N:12]=[C:26]1[CH3:27]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 89648267HCID 89648267, compound

Product 1

HCID 71610559HCID 71610559, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To a refluxed solution of N-(2,3-dichlorobenzyl)-6-morpholino-3-nitropyridin-2-amine (1.15 g, 3 mmol) in CH3COOH (100 mL) was added iron powder (504 mg, 9 mmol) in portions. The mixture was then refluxed for 16 h and cooled to room temperature. It was filtered and the filtrate was concentrated in vacuo. The residue was then purified by chromatography on silica gel eluting with EtOAc/Pet ether=1/1 to afford the desired product as a pale solid (352 mg, 30%). LC/MS: MS (ES+) m/e 377 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.41 (s, 3H), 3.36 (t, J=4.8 Hz, 4H), 3.67 (t, J=4.8 Hz, 4H), 5.46 (s, 2H), 6.63 (d, J=8.1 Hz, 1H), 6.72 (d, J=8.7 Hz, 1H), 7.28 (t, J=8.1 Hz, 1H), 7.59 (d, J=8.1 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H).

Workup

  1. temperatureThe mixture was then refluxed for 16 h
  2. filtrationIt was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was then purified by chromatography on silica gel eluting with EtOAc/Pet ether=1/1

Sources & evidence

ORD record
ord-b91ae7274291417abed391520c073d65
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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