6-Aminohexanoic Acid → 6-(4-Nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)hexanoic acid

HRID 1413347Notes

Reaction equation

HRID 1413347 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]>>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:10](=[O:11])[C:5]=12)=[O:9])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 216313-Nitrophthalic anhydride

Product 1

HCID 3035826-(4-Nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)hexanoic acidYield 93.1%

Procedure

The starting material used in the above example can be prepared as follows: 3.86 g (0.02 mol) of 3-nitrophthalic anhydride and 2.9 g (0.022 mol) of 6-aminocaproic acid are heated under reflux for 8 hours and then evaporated. The solid residue is stirred with water, filtered off with suction and dried for 24 hours at 80° C. 5.7 g (93% of theory) of 6-(3-nitrophthalimidyl)-caproic acid are obtained; melting point 148°-150° C. IR spectrum (CH2Cl2): 1790 and 1725 cm-1 (CO--N--CO); 1550 and 1370 cm-1 (NO2).

Workup

  1. customcan be prepared
  2. temperatureunder reflux for 8 hours
  3. customevaporated
  4. filtrationfiltered off with suction
  5. customdried for 24 hours at 80° C

Sources & evidence

ORD record
ord-b5959acc32a54984928bc0858f3dc033
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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