3-Propylaniline → HCID 19829931, compound

HRID 1493609

Reaction equation

HRID 1493609 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])[CH2:2][CH3:3].C(=O)(O)[O-].[Na+].Cl[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CCOCC>[CH3:21][O:20][C:18](=[O:19])[CH2:17][NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([CH2:1][CH2:2][CH3:3])[CH:5]=1

Participants

5

Reactant 3

HCID 60563-PropylanilineHCID 7295Methyl chloroacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 19829931HCID 19829931, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-n-Propyl-aniline (20 g, 148 mmol), sodium bicarbonate (24.9 g, 296 mmol) and methyl chloroacetate (24.0 g, 221 mmol) were mixed under nitrogen and stirred at 80°-90° C. for 24 h. The cooled reaction was poured into ether (100 ml) and filtered. The filtrate was washed with water (100 ml), dilute hydrochloric acid (100 ml) and water (100 ml), then dried and concentrated in vacuo. The oily product (21.2 g) was distilled on the Kugelrohr collecting the fraction boiling at 160°/0.35 mmHg to give the title compound (Intermediate 32) as a colourless liquid which solidified into a pale yellow, low melting solid (16.1 g, 53%).

Workup

  1. customThe cooled reaction
  2. filtrationfiltered
  3. washThe filtrate was washed with water (100 ml), dilute hydrochloric acid (100 ml) and water (100 ml)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. distillationThe oily product (21.2 g) was distilled on the Kugelrohr
  7. customcollecting the fraction boiling at 160°/0.35 mmHg

Sources & evidence

ORD record
ord-834a1ce188ab48e48d7cd9f817d0fb93
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Linked notes

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