Hydrochloric Acid → HCID 19064849, compound

HRID 1487222Notes

Reaction equation

HRID 1487222 reaction equation
[OH-:1].[Na+].[O:3]1[C:14]2[C:10]3[NH:11][C:12](=[O:13])[C:9]=3[CH:8]=[CH:7][C:6]=2[O:5][CH2:4]1.OO.Cl>O>[NH2:11][C:10]1[C:14]2[O:3][CH2:4][O:5][C:6]=2[CH:7]=[CH:8][C:9]=1[C:12]([OH:1])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86699690HCID 86699690, compound

Product 1

HCID 19064849HCID 19064849, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium hydroxide (4.6 g, 115 mmol) in water (35 mL) was added the Intermediate from Step C (2.35 g, 14.4 mmol). A solution of hydrogen peroxide (30%, 21 mL) was then added over 30 minutes. The reaction was neutralized to pH 7 by the addition of diluted hydrochloric acid (1N). The precipitate was collected and dried to afford the product 4-aminobenzo[d][1,3]dioxole-5-carboxylic acid (1.68 g, yield 64%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.40-7.42 (d, 1H, J=8.4 Hz), 6.25-6.27 (d, 1H, J=8.4 Hz), 6.04 (s, 2H).

Workup

  1. customThe precipitate was collected
  2. customdried

Sources & evidence

ORD record
ord-3a6811ca67b64ae3b08cf4c022c26100
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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