Potassium Hydroxide → HCID 20135076, compound

HRID 580413Notes

Reaction equation

HRID 580413 reaction equation
[OH-].[K+].C[O:4][C:5]([CH:7]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:12][C:11]2[C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=[CH:25][C:10]=2[NH:9][C:8]1=[O:30])=[O:6]>CO.O1CCOCC1>[C:5]([CH:7]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:12][C:11]2[C:22]([C:26]([F:28])([F:29])[F:27])=[CH:23][CH:24]=[CH:25][C:10]=2[NH:9][C:8]1=[O:30])([OH:6])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20135091HCID 20135091, compound

Product 1

HCID 20135076HCID 20135076, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred warm solution of 58.0 g (0.88 mol) of potassium hydroxide (85%) in 500 ml of methanol was added portionwise 81.7 g (0.21 mol) of 1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one - most of the solid dissolved. The mixture was diluted with 100 ml of dioxane and the resulting solution was refluxed for 6 hours. After standing overnight at room temperature, about 50% of the solvent was removed on a rotary evaporator and the residue was diluted with 4 liters of cold water. The insoluble material was filtered and dried (10 g) and the filtrate was cooled and treated portionwise with 270 ml of acetic acid to give a colorless granular solid. The latter was filtered, washed with cold water and dried in a desicator; yield 69.0 g, melting point 179°-181° C. (s. 128° C.).

Workup

  1. dissolutiondissolved
  2. temperaturethe resulting solution was refluxed for 6 hours
  3. customabout 50% of the solvent was removed on a rotary evaporator
  4. additionthe residue was diluted with 4 liters of cold water
  5. filtrationThe insoluble material was filtered
  6. customdried (10 g)
  7. temperaturethe filtrate was cooled
  8. additiontreated portionwise with 270 ml of acetic acid
  9. customto give a colorless granular solid
  10. filtrationThe latter was filtered
  11. washwashed with cold water
  12. customdried in a desicator
  13. customyield 69.0 g, melting point 179°-181° C. (s. 128° C.)

Sources & evidence

ORD record
ord-c8e6c0582e694280a02b118971192840
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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