Barium hydroxide, octahydrate → HCID 19040658, compound

HRID 1683769Notes

Reaction equation

HRID 1683769 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10](C)[CH2:11][CH2:12][C:6]=2[C:5]([C:14]#N)=[CH:4][CH:3]=1.[OH2:16].[OH2:17].O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>C(O)C.O.CO.C(=O)=O>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[C:5]([C:14]([OH:17])=[O:16])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 17749109Barium hydroxide, octahydrateHCID 19040669HCID 19040669, compound

Product 1

HCID 19040658HCID 19040658, compound

Reagents, catalysts & solvents 4

HCID 280Carbon DioxideSolventHCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine-6-carbonitrile, prepared as in Example 12, (1.5 g, 6.8 mmol) in ethanol (25 ml) was treated with barium hydroxide octahydrate (2.6 g, 8.1 mmol) and water (25 ml) and heated to reflux for 94 hours. The mixture was cooled, diluted with water, ethanol and methanol, saturated with carbon dioxide and filtered. The filtrate was treated with Dry Ice to pH 5-6 and filtered. The filtrate was concentrated and extracted with ethyl acetate-ethyl ether and ethyl ether. The aqueous phase was treated with toluene, concentrated and the residue triturated with ethyl ether to give 9-chloro-2,3,4,5-tetrahydro-1H-3-benzazepine-6-carboxylic acid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 94 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. additionThe filtrate was treated with Dry Ice to pH 5-6
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. extractionextracted with ethyl acetate-ethyl ether and ethyl ether
  9. additionThe aqueous phase was treated with toluene
  10. concentrationconcentrated
  11. customthe residue triturated with ethyl ether

Sources & evidence

ORD record
ord-cd7c462d527a4324b5bc1d317473dd93
Source dataset
uspto-grants-1997_06
Patent number
US05639748

Reaction notes

Loading…