Hydrochloric Acid → 6-Amino-2,3-dimethoxybenzoic acid hydrochloride

HRID 525955Notes

Reaction equation

HRID 525955 reaction equation
C(OC([NH:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([O:18][CH3:19])[C:12]([O:20][CH3:21])=[CH:11][CH:10]=1)=O)(C)(C)C.[ClH:22].O1CCOCC1>>[ClH:22].[NH2:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([O:18][CH3:19])[C:12]([O:20][CH3:21])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 144163466-((Tert-butoxycarbonyl)amino)-2,3-dimethoxybenzoic acid

Product 1

HCID 1317355906-Amino-2,3-dimethoxybenzoic acid hydrochlorideYield 91%

Procedure

6-((tert-Butoxycarbonyl)amino)-2,3-dimethoxybenzoic acid (39 g, 131 mmol) was treated with HCl in dioxane (4N, 300 mL, 1200 mmol) at r.t. and the mixture was stirred at r.t. for 3 h. LCMS indicated completion of the reaction. The solid was collected by filtration, washed with ethyl ether and dried to afford 6-amino-2,3-dimethoxybenzoic acid, Hydrochloride (28.5 g, 120 mmol, 91% yield) as a white solid. LCMS: (M+H)+: 198.2.

Workup

  1. customcompletion of the reaction
  2. filtrationThe solid was collected by filtration
  3. washwashed with ethyl ether
  4. customdried

Sources & evidence

ORD record
ord-daed9a45092c45948e7a8e5ecbbb5f3d
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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