HCID 69557857, compound → HCID 69557371, compound

HRID 2121595Notes

Reaction equation

HRID 2121595 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-a0f1827847a546349c1d31cdecc0dd49
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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