Sodium Hydroxide → 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoic acid

HRID 249162Notes

Reaction equation

HRID 249162 reaction equation
[OH-].[Na+].[CH:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[N:8]([CH2:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([O:24]C)=[O:23])[C:7]=2[CH:6]=[CH:5][CH:4]=1>O1CCOCC1.CO>[CH:14]1[C:10]2[CH2:11][CH2:12][C:13]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=3[N:8]([CH2:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([OH:24])=[O:23])[C:9]=2[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19024806methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoate

Product 1

HCID 190248733-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoic acidYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

1N aqueous solution of sodium hydroxide (9 ml) was added to a solution of methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoate (1.06 g) in a mixture of 1,4-dioxane (25 ml) and methanol (15 ml) at 25° C. The mixture was stirred at 25° C. for 3 hours, and then at 50° C. for 30 minutes. After evaporation of the solvent, the residue was partitioned between ethyl acetate and 0.1N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated to give 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoic acid (1.01 g) as powder.

Workup

  1. waitat 50° C. for 30 minutes
  2. customAfter evaporation of the solvent
  3. customthe residue was partitioned between ethyl acetate and 0.1N hydrochloric acid
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-7cd6604b53ae436bae4087f1e89d673a
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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