Nitric Acid → Methyl 3,5-dimethyl-4-nitrothiophene-2-carboxylate

HRID 978931Notes

Reaction equation

HRID 978931 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9].[N+:12]([O-])([OH:14])=[O:13].C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:1][C:2]1[C:6]([N+:12]([O-:14])=[O:13])=[C:5]([CH3:7])[S:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 20201092Methyl 3,5-dimethylthiophene-2-carboxylate

Product 1

HCID 20201108Methyl 3,5-dimethyl-4-nitrothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a well stirred, chilled (0°) solution of 51.4 g (0.3 mol) of methyl 3,5-dimethylthiophene-2-carboxylate in 200 ml of glacial acetic acid are added dropwise over a period of 40 minutes, a mixture of 30 ml of fuming nitric acid (specific gravity=1.5) and 120 ml of acetic anhydride. After the addition is completed the resulting brown solution is stirred a further two hours at 5° and then poured into 3000 ml of ice water.

Workup

  1. additionare added dropwise over a period of 40 minutes
  2. additionAfter the addition
  3. stirringis stirred a further two hours at 5°

Sources & evidence

ORD record
ord-8293cf00bcc04a7f811d2e6861523a79
Source dataset
uspto-grants-1987_05
Patent number
US04666502

Reaction notes

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