Acetic Acid → HCID 14502055, compound

HRID 231862Notes

Reaction equation

HRID 231862 reaction equation
C(N(CC)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1(O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:5])C.C(O)(=[O:34])C>[Zn]>[CH2:27]([N:24]([CH2:25][CH3:26])[CH2:23][CH2:22][N:13]1[CH:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:4]([OH:5])=[O:34])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:21])[CH3:28]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 14502053HCID 14502053, compound

Product 1

HCID 14502055HCID 14502055, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To a solution of 2.18 g of Compound 29 in 25 ml of acetic acid was added 5 g of zinc powders activated by washing with 2N-hydrochloride. After heating at reflux for 3.5 hours, the mixture was filtered and concentrated under reduced pressure. To the residue was added 20 ml of water, and pH was adjusted to 7 with 10N-sodium chloride solution. Then, filtration was performed and the mother liquor was concentrated under reduced pressure. The residue was subjected to HP-10 high porous polymer column-column chromatography (eluting solvent, water:methyl alcohol=1:3). A major fraction was concentrated to dryness under reduced pressure to give 1.56 g of 2-[2-(2-diethylaminoethyl)isoindolin-1-on-3-yl]benzoic acid (Compound 27).

Workup

  1. washby washing with 2N-hydrochloride
  2. temperatureAfter heating
  3. temperatureat reflux for 3.5 hours
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added 20 ml of water, and pH
  7. filtrationThen, filtration
  8. concentrationthe mother liquor was concentrated under reduced pressure
  9. washThe residue was subjected to HP-10 high porous polymer column-column chromatography (eluting solvent, water:methyl alcohol=1:3)
  10. concentrationA major fraction was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-10692b0d15f64fffa261e2e3ff53781c
Source dataset
uspto-grants-1989_07
Patent number
US04849441

Reaction notes

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