Water → 2-(3-chloropropoxy)aniline

HRID 567471Notes

Reaction equation

HRID 567471 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[Cl:11][CH2:12][CH2:13][CH2:14]Br.O>CN(C)C=O>[Cl:11][CH2:12][CH2:13][CH2:14][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 58012-AminophenolHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydride

Product 1

HCID 100126432-(3-chloropropoxy)anilineYield 12.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of sodium hydride (11.0 g, 230 mmol of a 50% oil dispersion) in dimethylformamide (250 ml), under nitrogen, was added, dropwise, 2-aminophenol (25.0 g, 230 mmol) dissolved in dimethylformamide (125 ml). After complete addition, the reaction was stirred at ambient temperature for 1 hour, and then it was cooled to 5° C. (ice bath). 3-Chloro-1-bromopropane (36.2 g, 230 mmol) in dimethylformamide (50 ml) was added, dropwise, so that the temperature did not go above 8° C. The reaction, was stirred for 4 hours and then permitted to stand at ambient temperature for 16 hours. The reaction was poured into water and extracted with ethyl acetate. The ethyl acetate was washed (water), dried (MgSO4), and the solvent concentrated to afford 25.4 g of a reddish, dark oil. About 12.0 g of the oil was chromatographed on HPLC columns. Concentration of the largest fractions gave 5.4 g of 2-(3-chloropropoxy)aniline as an oil.

Workup

  1. additionunder nitrogen, was added
  2. additionAfter complete addition
  3. temperatureit was cooled to 5° C. (ice bath)
  4. customdid not go above 8° C
  5. customThe reaction
  6. stirringwas stirred for 4 hours
  7. waitto stand at ambient temperature for 16 hours
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate was washed (water)
  10. dry with materialdried (MgSO4)
  11. concentrationthe solvent concentrated
  12. customto afford 25.4 g of a reddish, dark oil
  13. customAbout 12.0 g of the oil was chromatographed on HPLC columns

Sources & evidence

ORD record
ord-2cb3f8af5d864d2982f9255f799c4262
Source dataset
uspto-grants-2001_01
Patent number
USRE037029E1

Reaction notes

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