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

HRID 5883Notes

Reaction equation

HRID 5883 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, extracted with ethyl acetate, 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. extractionextracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-1b8a2b34a645485ea55d1706e0d72126
Source dataset
uspto-grants-1993_09
Patent number
US05246942

Reaction notes

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