Methanol → HCID 69557371, compound

HRID 1634554Notes

Reaction equation

HRID 1634554 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.CO>C(O)(=O)C.[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 2

HCID 887MethanolHCID 69557857HCID 69557857, compound

Product 1

HCID 69557371HCID 69557371, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

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) an14 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 saturate 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
  8. concentrationsaturate aq NaCl
  9. customSeparate the organic layer
  10. dry with materialdry over Na2SO4
  11. filtrationfilter
  12. concentrationconcentrate

Sources & evidence

ORD record
ord-8573ffd33e474edd8924cf2f69667b5b
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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