Sodium Hydroxide → HCID 19853881, compound

HRID 1723060Notes

Reaction equation

HRID 1723060 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-dc24f7d8ab10493eb21273e7ad0b3568
Source dataset
uspto-grants-1989_08
Patent number
US04859683

Reaction notes

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