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

HRID 1019100

Reaction equation

HRID 1019100 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-df7adffb19e44fa2ae182c02f57d6391
Source dataset
uspto-grants-2002_11
Patent number
US06486193B2

Linked notes

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