Water → 4-Iodo-2-methyl-6-nitroaniline

HRID 470366Notes

Reaction equation

HRID 470366 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1[NH2:4].CC([O-])=O.[Na+].[I:17]Cl.O>C(O)(=O)C>[I:17][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]([NH2:4])=[C:2]([CH3:1])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 112982-Methyl-6-nitroanilineHCID 24640Iodine chlorideHCID 517045Sodium Acetate

Product 1

HCID 248996464-Iodo-2-methyl-6-nitroanilineYield 98.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-methyl-6-nitroaniline (106.5 g, 0.7 mol) and NaOAc (63.2 g, 0.77 mol) in acetic acid (525 mL) was added a solution of ICl (125 g, 0.77 mol) in acetic acid (350 mL). The mixture was heated at 80° C. for 50 min and poured into H2O (2100 mL). After stayed at the room temperature for 16 h, the mixture was filtered to furnish yellow solid that was washed with H2O (3×350 mL). Drying under reduced pressure at 40° C. for 48 h afforded the title compound (191 g, 98%). 1H NMR (CDCl3) δ 2.22 (s, 3H), 6.20 (br s, 2H NH), 7.53 (s, 1H), 8.34 (s, 1H). ESI-MS m/z 279 (MH+).

Workup

  1. filtrationthe mixture was filtered
  2. customto furnish yellow solid
  3. washthat was washed with H2O (3×350 mL)
  4. customDrying under reduced pressure at 40° C. for 48 h

Sources & evidence

ORD record
ord-7c2f8cecb64f4d928d810c26cf9cf804
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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