Sodium Carbonate → 8-Amino-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

HRID 2406330Notes

Reaction equation

HRID 2406330 reaction equation
Br[C:2]1[C:11](Br)=[C:10]([N+:13]([O-])=O)[C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].O>[NH2:13][C:10]1[C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]([C:16]([OH:18])=[O:17])=[CH:2][CH:11]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 205447596,7-Dibromo-8-nitro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Product 1

HCID 211934708-Amino-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acidYield 259.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

An autoclave container was charged water (4.0 mL), 6,7-dibromo-8-nitro-1,4-benzodio-xane-5-carboxylic acid (1.9 g, 0.5 mmol), saturated sodium carbonate (1.0 mL), and Pd/C (500 mg). The mixture was hydrogenated at 40 kg/cm2 at 50° C. for overnight. It was then filtered and the filtrate was treated with hydrochloric acid (3.0 mL). The suspension was filtered and the solid was washed with water to afford the title compound (253 mg, 26%). LCMS: ESI (3 minute run), m/z=196 [M+1]+; Retention time: 0.30 minute.

Workup

  1. filtrationIt was then filtered
  2. additionthe filtrate was treated with hydrochloric acid (3.0 mL)
  3. filtrationThe suspension was filtered
  4. washthe solid was washed with water

Sources & evidence

ORD record
ord-ff18156f87124bc4b63d31aeb19970f1
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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