Triethylamine → HCID 12223910, compound

HRID 1199998Notes

Reaction equation

HRID 1199998 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].C(N(CC)CC)C>C1(C)C=CC=CC=1>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 12223910HCID 12223910, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Fluoronitrobenzene (28 g), 4-aminobutanol (18 g) and triethylamine (29 ml) were dissolved in toluene (100 ml) and heated at 100° for 6 hours. The organic phase was washed with water (50 ml) and then extracted with concentrated hydrochloric acid (2×50 ml). The combined acid extracts were diluted with water (100 ml), neutralised with concentrated aqueous ammonia and extracted with methylene chloride (3×50 ml). The organic extracts were combined, dried over Na2SO4, filtered and evaporated to leave the title compound as a dark red oil (41 g) which was used directly in the next step.

Workup

  1. temperatureheated at 100° for 6 hours
  2. washThe organic phase was washed with water (50 ml)
  3. extractionextracted with concentrated hydrochloric acid (2×50 ml)
  4. additionThe combined acid extracts were diluted with water (100 ml), neutralised with concentrated aqueous ammonia
  5. extractionextracted with methylene chloride (3×50 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-25b48274c2924a1eb84fb8ba5de4eaa0
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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