Ethanolamine → HCID 18387488, compound

HRID 2296617Notes

Reaction equation

HRID 2296617 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[CH2:13]([CH2:15][NH2:16])[OH:14]>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][NH:16][CH2:15][CH2:13][OH:14]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 27347702-Fluoro-5-nitrobenzaldehyde

Product 1

HCID 18387488HCID 18387488, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-fluoro-5-nitrobenzaldehyde (52.4 g, 0.31 mol) in absolute ethanol (500 ml) was added ethanolamine (18.93 g, 0.31 mol) and borane-pyridine complex (31.31 ml, 0.31 mol). The mixture was stirred for 48 h and then evaporated. The residue was acidified with 2.5N hydrochloric acid, extracted with methylene chloride (3×150 ml), and the extracts were discarded. The aqueous phase was basified with 25% aqueous sodium hydroxide and extracted with methylene chloride (4×200 ml). These extracts were washed with saturated brine solution, dried over magnesium sulfate and evaporated to give yellow crystals (37.67 g, 57%), m.p. 98.5-99.5° C.

Workup

  1. customevaporated
  2. extractionextracted with methylene chloride (3×150 ml)
  3. extractionextracted with methylene chloride (4×200 ml)
  4. washThese extracts were washed with saturated brine solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d9b1db72bdf34a3c84da1b7fead8faf2
Source dataset
uspto-grants-2002_12
Patent number
US06489322B1

Reaction notes

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