2-Chloro-6-methyl-4-nitroaniline → HCID 1481998, compound

HRID 1823919Notes

Reaction equation

HRID 1823919 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([CH3:12])[C:3]=1[NH2:4].[N:13]([O-])=O.[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]2[C:3]=1[NH:4][N:13]=[CH:12]2

Participants

5

Reactant 2

HCID 27334602-Chloro-6-methyl-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 1481998HCID 1481998, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 2-chloro-6-methyl-4-nitroaniline (5.49 g, 29.4 mmole) in acetic acid (150 mL) was added sodium nitrite (2.03 g, 29.4 mmole) pre-dissolved in water (5 mL). The resulting brown slurry was stirred overnight at room temperature, then at 60° C. for a further 4 hours. The bulk of the solvent was removed by evaporation in-vacuo and the resulting black residue re-dissolved in EtOAc (100 mL) and washed in brine (2×70 mL). The organic layer was dried (MgSO4), filtered and concentrated to give a mixture of starting material and product 91 mg(1.49 g). The crude mixture was taken through to the next step; 1H NMR (400 MHz, DMSO) δ 8.25(1H, s), 8.50(1H, s), 8.85(1H, s), 14.30(1H, br s).MS (ES+): m/e=198 (minus Boc).

Workup

  1. waitat 60° C. for a further 4 hours
  2. customThe bulk of the solvent was removed by evaporation in-vacuo
  3. dissolutionthe resulting black residue re-dissolved in EtOAc (100 mL)
  4. washwashed in brine (2×70 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give

Sources & evidence

ORD record
ord-d7844be1f8724678841c25cbc7d8bd1e
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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