Water → 2-Amino-5-(diethylamino)toluene

HRID 436552

Reaction equation

HRID 436552 reaction equation
[NH:1]([C:5]1[CH:15]=[CH:14][C:8]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:7][C:6]=1[CH3:16])C(C)=O.O.[OH-].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:5]1[CH:15]=[CH:14][C:8]([N:9]([CH2:10][CH3:11])[CH2:12][CH3:13])=[CH:7][C:6]=1[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 222177N-[4-(diethylamino)-2-methylphenyl]acetamide

Product 1

HCID 673642-Amino-5-(diethylamino)toluene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

22g of 4-acetamino-3-methyl-(N,N-diethyl)aniline were dissolved in 30g of 50% sulfuric acid and stirred and reacted for 5 hours at 80° to 100° C. Then, after 50g of water had been added thereto, the reaction mixture was neutralized with 30% sodium hydroxide and extracted with 150ml of benzole. The benzole used was distilled off from the extract to obtain 14.4g of 4-amino-3-methyl-(N,N-diethyl)aniline. The product was distilled for purification under a reduced pressure of 130° C/2mmHg to obtain 13.5g of 4-amino-3-methyl-(N,N-diethyl) aniline. The free amine was dissolved in 100ml of diethyl ether and was converted to the hydrogen chloride salt thereof by introducing dry hydrogen chloride gas into the system. Then, the salt was filtered out and dried to obtain 17.7g of 4-amino-3-metnyl-(N,N-diethyl)aniline hydrochloride.

Workup

  1. customreacted for 5 hours at 80° to 100° C
  2. extractionextracted with 150ml of benzole
  3. distillationThe benzole used was distilled off from the
  4. extractionextract

Sources & evidence

ORD record
ord-0121c25b959b420c9d20d0d33ae2a37a
Source dataset
uspto-grants-1977_02
Patent number
US04009205

Linked notes

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