4-Chloro-2-nitroaniline → HCID 21901091, compound

HRID 336442Notes

Reaction equation

HRID 336442 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[N:12]([O-])=O.[Na+].[Sn](Cl)Cl>Cl.O>[ClH:1].[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][NH2:12])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 69794-Chloro-2-nitroanilineHCID 24479Stannous ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 21901091HCID 21901091, compoundYield 116.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-2-nitroaniline (40 g, 0.23 mol) prepared in Preparation 13 was dissolved in 12N hydrochloric acid (100 mL). Sodium nitrite (16 g, 0.23 mol) dissolved in water (50 mL) was slowly added in drops thereto at 0° C., and the mixture was stirred for 30 min at 0° C. to room temperature. The reaction mixture was cooled to 0° C., tin (II) chloride (132 g, 0.70 mol) dissolved in 12N hydrochloric acid (100 mL) was slowly added in drops thereto, and the mixture was stirred for 3 h at 0° C. to room temperature. The resulting yellow solid was filtered, washed with a small amount of 6N HCl, and dried to give the title compound (30 g, Yield 63%).

Workup

  1. additionwas slowly added in drops
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. additionwas slowly added in drops
  4. stirringthe mixture was stirred for 3 h at 0° C. to room temperature
  5. filtrationThe resulting yellow solid was filtered
  6. washwashed with a small amount of 6N HCl
  7. customdried

Sources & evidence

ORD record
ord-ef7661c19ace4a3aaf3cf7e4cd14c1ab
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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