Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate → Lithium benzomorpholine-2-carboxylate

HRID 253109

Reaction equation

HRID 253109 reaction equation
O.[OH-].[Li+:3].[O:4]1[CH:9]([C:10]([O:12]CC)=[O:11])[CH2:8][NH:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2>O.O1CCOCC1>[O:4]1[CH:9]([C:10]([O-:12])=[O:11])[CH2:8][NH:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2.[Li+:3]

Participants

5

Reactant 2

HCID 31090Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 69210254Lithium benzomorpholine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of lithium hydroxide monohydrate (1.43 g, 34.2 mmol) in water (50 mL) was added to a solution of ethyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (3.55 g, 17.1 mmol) in dioxane (50 mL), and the mixture was stirred at 25° C. for 21 h. The reaction mixture was concentrated to afford the title compound. MS m/z: 180 (M+1 of acid).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-638921f9b32b42dea4acc22d5e5b8562
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Linked notes

Loading…