HCID 69557857, compound → HCID 69557371, compound

HRID 1792265Notes

Reaction equation

HRID 1792265 reaction equation
[CH3:1][C:2]1([CH3:28])[CH:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:6]([CH3:15])=[C:5]([N+:16]([O-])=O)[C:4]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH3:19])[CH2:3]1>C(O)(=O)C.CO.[Fe]>[NH2:16][C:5]1[C:4]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH3:19])[CH2:3][C:2]([CH3:1])([CH3:28])[CH:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:6]=1[CH3:15]

Participants

5

Reactant 1

HCID 69557857HCID 69557857, compound

Product 1

HCID 69557371HCID 69557371, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Add iron powder (7.0 g) to a solution of 6-methyl-3-nitro-4-[benzylamino](2-pyridyl)(2,4,6-trimethylphenyl)amine (8.75 g, 23.2 mmol) in acetic acid (14 mL) and MeOH (70 mL). Heat the resulting mixture at 70° C. for 1 h, cool to ambient temperature, and filter through a pad of celite. Evaporate the filtrate to dryness under reduced pressure. Treat he residue with 1N aq NaOH and extract with EtOAc. Wash the EtOAc extract with water and saturated aq NaCl. Separate the organic layer, dry over Na2SO4, filter, and concentrate to obtain the title compound as a brown solid which is used without further purification.

Workup

  1. temperaturecool to ambient temperature
  2. filtrationfilter through a pad of celite
  3. customEvaporate the filtrate to dryness under reduced pressure
  4. additionTreat he residue with 1N aq NaOH
  5. extractionextract with EtOAc
  6. washWash the EtOAc
  7. extractionextract with water and saturated aq NaCl
  8. customSeparate the organic layer
  9. dry with materialdry over Na2SO4
  10. filtrationfilter
  11. concentrationconcentrate

Sources & evidence

ORD record
ord-93a0e0392bfb41d1a4ce35af9bec7f30
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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