Sodium Carbonate → 4-Amino-n-sec-butyl-n-ethyl-3-toluidine

HRID 1977539Notes

Reaction equation

HRID 1977539 reaction equation
[CH:1]([N:5]([CH2:15][CH3:16])[C:6]1[CH:11]=[CH:10][C:9]([N:12]=O)=[C:8]([CH3:14])[CH:7]=1)([CH2:3][CH3:4])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].C1C(=NNC2C=CC(/C=C/C3C=CC(NN=C4C=CC(=O)C=C4)=CC=3S([O-])(=O)=O)=C(S([O-])(=O)=O)C=2)C=CC(=O)C=1.[Na+].[Na+]>CO.Cl.[Fe]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH2:15][CH3:16])=[CH:7][C:8]=1[CH3:14]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 21993243n-Sec-butyl-n-ethyl-4-nitroso-3-toluidineHCID 178516258HCID 178516258, compound

Product 1

HCID 219932414-Amino-n-sec-butyl-n-ethyl-3-toluidine

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst2×HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

A suspension of iron powder (8.34 g) in methanol (60 ml) and hydrochloric acid (20 ml) was stirred at reflux for 15 mins. A solution of the product from Stage 1d (11 g) in methanol (60 ml) was added dropwise over 15 mins and refluxing continued for 3 hours. Sodium carbonate was added until no soluble iron remained and the solution was alkaline to Brilliant Yellow paper. The hot reaction mixture was filtered and the solvent removed under reduced pressure to give the product as a brown oil.

Workup

  1. temperatureat reflux for 15 mins
  2. temperaturerefluxing
  3. filtrationThe hot reaction mixture was filtered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-07c4917aba174374bbdaf7185009b95a
Source dataset
uspto-grants-2001_05
Patent number
US06235096B1

Reaction notes

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