6-Aminohexanoic Acid → 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acid

HRID 1385046Notes

Reaction equation

HRID 1385046 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])(OCC)=O>O>[C:22]1(=[O:31])[N:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]12

Participants

5

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 10340Sodium CarbonateHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 781851,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 6-aminohexanoic acid (6-aminocaproic acid) (8.0 g, 60 mmol) and water (100 mL). Add sodium carbonate (6.84 g, 64 mmol) and N-carbethoxyphthalimide (14.0 g, 64 mmol). After 1.5 hours, extract the reaction mixture with ethyl acetate (100 mL). Cool the aqueous layer in an ice bath and acidify using concentrated hydrochloric acid to give a solid. Collect the solid by filtration, rinse with water, and dry to give 6-phthalimidohexanoic acid (12.7 g, 80% yield).

Workup

  1. extractionextract the reaction mixture with ethyl acetate (100 mL)
  2. temperatureCool the aqueous layer in an ice bath
  3. customto give a solid
  4. customCollect the solid
  5. filtrationby filtration
  6. washrinse with water
  7. customdry

Sources & evidence

ORD record
ord-24c0d446abe04e09a99ab24addf5d4d3
Source dataset
uspto-grants-2001_07
Patent number
US06262080B1

Reaction notes

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