3,4-Dimethylaniline → N-2-heptyl-3,4-xylidine

HRID 443775Notes

Reaction equation

HRID 443775 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1.[CH3:10][C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[H][H]>[Pt].C1C2C(=CC=CC=2)C=CC=1S(O)(=O)=O>[CH3:10][CH:11]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 72483,4-DimethylanilineHCID 80512-HeptanoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 23465421N-2-heptyl-3,4-xylidineYield 99.4%

Reagents, catalysts & solvents 2

HCID 84202-Naphthalenesulfonic acidCatalystHCID 23939PlatinumCatalyst

Procedure

3,4-Xylidine (24.2 grams; 0.2 mole), 2-heptanone (50.2 grams, 0.44 mole), 2-naphthalenesulfonic acid (0.9 g) and 5% of platinum on carbon (1.2 gms) were charged to a Parr reaction bottle and treated with hydrogen at 70° C. and a hydrogen pressure of 41-60 psig. The theoretical amount of hydrogen was consumed within 15 minutes. The mixture was held an additional 35 minutes, producing 43.6 g of N-2-heptyl-3,4-xylidine. The above sample analyzed 100% pure, corresponding to a yield of 99%.

Workup

  1. customThe theoretical amount of hydrogen was consumed within 15 minutes

Sources & evidence

ORD record
ord-685f4cf172a7426384fea0e79580cb86
Source dataset
uspto-grants-1981_04
Patent number
US04261926

Reaction notes

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