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

HRID 1876304Notes

Reaction equation

HRID 1876304 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-])=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 24268Sodium NitrateHCID 24479Stannous Chloride

Product 1

HCID 21901091HCID 21901091, compoundYield 116.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

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

Workup

  1. additionwas slowly added in drops
  2. customwas lowered to 0° C.
  3. additionwas slowly added in drops
  4. stirringThe mixture was stirred for 3 h at 0° C.˜room temperature
  5. filtrationThe resulting yellow solid was filtered
  6. washwashed with a small quantity of 6N HCl
  7. customdried

Sources & evidence

ORD record
ord-a690b2da850541548308c67b809a001f
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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