Ethanol → 7-Amino-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

HRID 2052639Notes

Reaction equation

HRID 2052639 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:13]=1)([O-])=O.C(O)C.[H][H]>[Ni].O>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:13]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 124645337-Nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 205447527-Amino-2,3-dihydro-1,4-benzodioxine-5-carboxylic acidYield 75.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

56 g of 7-nitro-1,4-benzodioxane-5-carboxylic acid, 560 ml of absolute ethanol and Raney nickel were introduced into an autoclave and then hydrogen under a pressure of 65 kg/cm2 was introduced while heating. The mixture was then agitated at 60° C. and treated with a solution of 50 ml of soda lye in 450 ml of water. The solution was filtered and treated with 50 ml of hydrochloric acid. The precipitate was dried off, washed with water and dried. 36.5 g of 7-amino-1,4-benzodioxane-5-carboxylic acid were obtained (M.P.: 220° C.; yield: 75%).

Workup

  1. temperaturewhile heating
  2. filtrationThe solution was filtered
  3. additiontreated with 50 ml of hydrochloric acid
  4. customThe precipitate was dried off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-6cfad75cf2224f6f8bb251d48caef35d
Source dataset
uspto-grants-1980_01
Patent number
US04186135

Reaction notes

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