4-Methyl-2-nitroaniline → HCID 16495251, compound

HRID 2089560Notes

Reaction equation

HRID 2089560 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[N:12]([O-])=O.[Na+].[Sn](Cl)[Cl:17]>Cl.O>[ClH:17].[N+:9]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[NH:8][NH2:12])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 69784-Methyl-2-nitroanilineHCID 24479Stannous ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 16495251HCID 16495251, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The commercially available 4-methyl-2-nitro-phenylamine (40 g, 0.23 mol) was dissolved in 12N-hydrochloric acid (100 mL), to which sodium nitrite (16 g, 0.23 mol) dissolved in water (50 mL) was slowly added in drops at 0° C. The reaction mixture was stirred for 30 min at 0° C. After lowering the temperature of the reaction mixture to 0° C., tin (II) chloride (132 g, 0.70 mol) dissolved in 100 mL of 12N-hydrochloric acid was slowly added in drops thereto. The reaction 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 at 0° C
  2. customto 0° C.
  3. additionwas slowly added in drops
  4. stirringThe reaction 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-20eafec877cf456e994d6879a6990a25
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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