Sodium → 1-Amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid

HRID 1032839Notes

Reaction equation

HRID 1032839 reaction equation
[Na].C([NH:5][C:6]1[C:14]2[CH:13]3[CH2:15][CH2:16][CH2:17][CH2:18][CH:12]3[O:11][C:10]=2[C:9]([C:19]([O:21]C)=[O:20])=[CH:8][C:7]=1[Cl:23])(=O)C>CO.[OH-].[Na+]>[NH2:5][C:6]1[C:14]2[CH:13]3[CH2:15][CH2:16][CH2:17][CH2:18][CH:12]3[O:11][C:10]=2[C:9]([C:19]([OH:21])=[O:20])=[CH:8][C:7]=1[Cl:23]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 15136047Methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

Product 1

HCID 151360481-Amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 0.3 g of sodium in 15 ml methanol is added 0.6 g of methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate. Stirring is continued at 60° C. for two days. This is then diluted with 5 ml 1N sodium hydroxide and stirring continued at 60° C. overnight. The methanol is removed in vacuum, diluted with water, filtered, acidified with acetic acid, filtered, washed with water, dried over magnesium sulfate and evaporated to dryness to obtain 1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid. This is purified by crystallization from ethyl acetate/ether.

Workup

  1. stirringstirring
  2. waitcontinued at 60° C. overnight
  3. customThe methanol is removed in vacuum
  4. additiondiluted with water
  5. filtrationfiltered
  6. filtrationfiltered
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-5727320623114d259aa5a26ba5a7ae20
Source dataset
uspto-grants-1990_09
Patent number
US04959485

Reaction notes

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