Hydrochloric Acid → 3-Oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid

HRID 1184433Notes

Reaction equation

HRID 1184433 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([C:12]([O:14]C)=[O:13])=[CH:11][C:4]=2[NH:3]1.[Li+].[OH-].Cl>O1CCOCC1>[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([C:12]([OH:14])=[O:13])=[CH:11][C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 2974054Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Product 1

HCID 7061213-Oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 18 (1.0 mmol) in dioxane (4 mL) was added aqueous LiOH (1 M, 4 mL, 4.0 mmol). The solution was stirred at 23° C. for 1 h and then quenched with aqueous HCl (4 M, 2 mL, 8 mmol). The resulting solid was isolated by filtration, washed with water and dried in vacuo to give a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=12.81 (s, 1H), 10.88 (s, 1H), 7.48-7.54 (m, 2H), 7.01 (d, J=8.3 Hz, 1H), 4.67 ppm (s, 2H). ESI-MS: m/z 194.0 (M+H)+.

Workup

  1. customThe resulting solid was isolated by filtration
  2. washwashed with water
  3. customdried in vacuo
  4. customto give a white solid

Sources & evidence

ORD record
ord-4f0d84fe40aa469385cb2c6ba7695f11
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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