Sodium Hydroxide → HCID 19853881, compound

HRID 1650380Notes

Reaction equation

HRID 1650380 reaction equation
C([NH:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([O:18]C)=[O:17])=[CH:7][C:6]=1[Cl:20])(=O)C.[OH-].[Na+]>CO>[NH2:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([OH:18])=[O:17])=[CH:7][C:6]=1[Cl:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19853900HCID 19853900, compound

Product 1

HCID 19853881HCID 19853881, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5 g (16.8 mmol) of methyl 6-acetylamino-7-chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylate in 10 ml of methanol is added 10 ml of a 10% aqueous sodium hydroxide solution in a single portion at room temperature. The solution is heated to reflux and maintained for 2 hours. After cooling, methanol is removed in vacuo and the residue is diluted with water. The pH of this solution is adjusted to 7 with 1N HCl. The neutral solution is extracted with CH2Cl2 and the combined organic extracts are dried over MgSO4, filtered and concentrated. Flash chromatography (30% EtOAc/hexanes) provides 6-amino-7-chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux
  3. temperaturemaintained for 2 hours
  4. temperatureAfter cooling
  5. custommethanol is removed in vacuo
  6. additionthe residue is diluted with water
  7. extractionThe neutral solution is extracted with CH2Cl2
  8. dry with materialthe combined organic extracts are dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7f23ca2c6dbb41f8baf759512bd5305e
Source dataset
uspto-grants-1990_05
Patent number
US04924010

Reaction notes

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