HCID 178474037, compound → HCID 20186463, compound

HRID 2308953Notes

Reaction equation

HRID 2308953 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[C:9]([C:12](=[O:20])[C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:14][CH:15]=2)=[CH:10][CH:11]=1)(=[O:3])[CH3:2]>C(O)(=O)C.[Zn]>[C:1]([NH:4][CH:5]1[CH2:11][CH2:10][C:9]2[C:12](=[O:20])[CH:13]([CH2:16][C:17]([OH:19])=[O:18])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 178474037HCID 178474037, compound

Product 1

HCID 20186463HCID 20186463, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Zinc dust (5.3 g) is added in portions to a stirred suspension of the 7-acetylamino-1-oxo-benzocyclohepten-2-yl-acetic acid (6 g) in 80% aqueous acetic acid (70 ml), warmed at 100° C.; the stirring is continued for 1 hour. The inorganic materials are removed by filtration and washed with warm 80% aqueous acetic acid (70 ml).The eluates are collected and acetic acid is distilled off under vacuum. The residual aqueous phase is extracted with ethyl ether, the combined extracts are dried on Na2SO4 and the solvents are evaporated. The crude material is triturated with hexane-ethyl ether to give 7-acetylamino-1-oxo-benzocycloheptan-2-yl-acetic acid (5.1 g) m.p. 198° C.

Workup

  1. customThe inorganic materials are removed by filtration
  2. washwashed
  3. temperaturewith warm 80% aqueous acetic acid (70 ml).The eluates
  4. customare collected
  5. distillationacetic acid is distilled off under vacuum
  6. extractionThe residual aqueous phase is extracted with ethyl ether
  7. customthe combined extracts are dried on Na2SO4
  8. customthe solvents are evaporated
  9. customThe crude material is triturated with hexane-ethyl ether

Sources & evidence

ORD record
ord-e43ea65b60fc4d45b64288058c54ed3a
Source dataset
uspto-grants-1987_09
Patent number
US04692447

Reaction notes

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