3,4,5,6-Tetrahydrophthalic anhydride → HCID 86739141, compound

HRID 904783Notes

Reaction equation

HRID 904783 reaction equation
[C:1]12[C:10](=[O:11])[O:9][C:7](=O)[C:2]=1[CH2:3][CH2:4][CH2:5][CH2:6]2.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:28])=[C:17]([CH:27]=1)[O:18][CH:19]([CH2:24][CH2:25][CH3:26])[C:20](=[N:22][OH:23])[CH3:21]>C(O)(=O)C>[Cl:28][C:16]1[CH:15]=[CH:14][C:13]([N:12]2[C:10](=[O:11])[C:1]3[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=3[C:7]2=[O:9])=[CH:27][C:17]=1[O:18][CH:19]([CH2:24][CH2:25][CH3:26])[C:20](=[N:22][OH:23])[CH3:21]

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 86739142HCID 86739142, compound

Product 1

HCID 86739141HCID 86739141, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.52 g. of cyclohexene-1,2-dicarboxylic anhydride, 2.57 g. of 3-(5-amino-2-chlorophenoxy)-hexan-2-one oxime (nD25 =1.5506) and 8 ml. of acetic acid was refluxed for 2.5 hours and the reaction mixture was cooled to room temperature and the product was extracted with ethyl acetate and was washed with water and was dehydrated over sodium sulfate. The product was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 1:3) to obtain 3.53 g. of Compound No. 68 shown in Table 1.

Workup

  1. additionA mixture of 1.52 g
  2. extractionthe product was extracted with ethyl acetate
  3. washwas washed with water
  4. customThe product was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 1:3)
  5. customto obtain 3.53 g

Sources & evidence

ORD record
ord-0a55b87c1dcc4c179945840997fe4a7c
Source dataset
uspto-grants-1983_12
Patent number
US04420327

Reaction notes

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