Ethyl Acetate → HCID 11961186, compound

HRID 1970099Notes

Reaction equation

HRID 1970099 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[C@H:9]3[CH2:13][N:12]([CH3:14])[C:11](=[O:15])[C@H:10]3[C:4]=2[CH:3]=1.[OH-].[K+].C(OCC)(=[O:26])C>C(O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[C@@H:9]([CH2:13][NH:12][CH3:14])[C@H:10]([C:11]([OH:15])=[O:26])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 15640770HCID 15640770, compound

Product 1

HCID 11961186HCID 11961186, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of cis-1′-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (V) (2 gram, 6.7 mmol) in ethanol (20 mL), was added potassium hydroxide (3.8 g, 67 mmol). The reaction mixture was heated to reflux for 5 hours. The reaction mixture was evaporated and water was added (50 mL). The water phase was washed with diethyl ether (2×25 mL). The aqueous phase was acidified with concentrated hydrochloric acid to a pH between 5 and 6, resulting in a gum precipitate. Ethyl acetate was added (25 mL), which slowly dissolved the gum and resulted in the formation of fine crystals of the product. The crystals were filtered and dried to give trans-8-chloro-10,11-dihydro-11-[(methylamino)-methyl]-dibenz[b,f]oxepin-10-carboxylic acid (I) (1.1 g, 52%); mp 154.4° C.; 1H-NMR (399.87 MHz in MeOD relative to TMS) δ 2.09 (s, 3H), 2.45 and 2.66 (2×m, 2H), 3.23 (s, 1H), 3.50 (m, 1H), 3.92 (d, 1H), 6.96-7.20 (m, 6H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. customThe reaction mixture was evaporated
  4. additionwater was added (50 mL)
  5. washThe water phase was washed with diethyl ether (2×25 mL)
  6. customresulting in a gum precipitate
  7. dissolutionslowly dissolved the gum
  8. customresulted in the formation of fine crystals of the product
  9. filtrationThe crystals were filtered
  10. customdried

Sources & evidence

ORD record
ord-b3ce47960bfb4267b9237dd07d64a170
Source dataset
uspto-grants-2013_04
Patent number
US08426610B2

Reaction notes

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