2-Methyl-5-Nitroaniline → HCID 67494403, compound

HRID 1968934Notes

Reaction equation

HRID 1968934 reaction equation
Cl.[N:2]1[CH:7]=[C:6]([CH:8]=[CH:9][C:10](Cl)=[O:11])[CH:5]=[N:4][CH:3]=1.[CH3:13][C:14]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=1[NH2:16].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:13][C:14]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=1[NH:16][C:10](=[O:11])[CH:9]=[CH:8][C:6]1[CH:7]=[N:2][CH:3]=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 74442-Methyl-5-NitroanilineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 77139281HCID 77139281, compound

Product 1

HCID 67494403HCID 67494403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of the product of step 3 (2.05 g) in anhydrous dichloromethane (30 ml), a solution of 2-methyl-5-nitroaniline (3.04 g) and triethylamine (8 ml, excess allowed) in dichloromethane (15 ml) was added dropwise slowly in an ice-bath with the temperature no more than 5° C. After addition, the reaction was carried out for 30 min in an ice-bath, and then at room to temperature for 3 h. Completion of reaction was indicated by TLC. Potassium carbonate solution (10%) was added to the mixture. Then the mixture was extracted with EtOAc (20 ml*3). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to recover the solvent. The residue was purified on silica gel column (EtOAc/petroleum ether 4:1). The eluent was collected, concentrated under reduced pressure to give a yellow powdered solid.

Workup

  1. additionAfter addition
  2. waitat room to temperature for 3 h
  3. customCompletion of reaction
  4. extractionThen the mixture was extracted with EtOAc (20 ml*3)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto recover the solvent
  9. customThe residue was purified on silica gel column (EtOAc/petroleum ether 4:1)
  10. customThe eluent was collected
  11. concentrationconcentrated under reduced pressure
  12. customto give a yellow powdered solid

Sources & evidence

ORD record
ord-125f4960c91b435b966dc736ef854f8b
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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