6-Aminohexanoic Acid → Ninhydrin
Reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[OH-:10].[Na+].[C:12](OC(OC(OC(C)(C)C)=O)=O)(C)([CH3:14])[CH3:13].[O:27]1CCOCC1>>[CH:2]1[CH:13]=[C:12]2[C:14]([C:7]([OH:9])([OH:8])[C:6](=[O:27])[C:5]2=[CH:4][CH:3]=1)=[O:10]Participants
5
Procedure
To 13.12 g (100 mmol) of 6-aminohexanoic acid in 400 mL of dioxan at 0° C. was added 100 mL of 1M NaOH, and 24.01 g (110 mmol) of di-tert-butyl-pyrocarbonate. The resulting suspension was stirred at room temperature for 3 days, after which time it gave a negative ninhydrin test. The volume was then reduced under pressure to 100 mL, the mixture cooled to 0° C., covered with ethyl acetate, and acidified with 1M KHSO4 to pH 2-3. The product was extracted with ethyl acetate (3×150 mL), the organic phase washed with H2O (2×300 mL), dried (Na2SO4) and evaporated to a thick syrup. This was recrystallized from ethyl acetate/hexane, to give 20.40 g (88%), mp 39°-41° C. (lit14 mp 39.5° C.).
Sources & evidence
- ORD record
- ord-8c87b8c7d5874498a4067f8a722dc8df
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05552540
Reaction notes
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