Chloroacetyl chloride → Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate

HRID 417919Notes

Reaction equation

HRID 417919 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].C(N(CC)CC)C.Cl[CH2:21][C:22](Cl)=[O:23].[H-].[Na+]>C1COCC1>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]2[NH:1][C:22](=[O:23])[CH2:21][O:12][C:3]=2[CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 10845978Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using methyl 4-amino-3-hydroxybenzoate (2 g, 12 mmol), triethylamine (2.17 mL, 16 mmol) and chloroacetyl chloride (1.13 mL, 13 mmol) in THF (70 mL) followed by sodium hydride (1.0 g of a 60% suspension in oil, 24 mmol) to yield the title compound as a brown solid (2.33 g, 94%). δH (DMSO-d6) 3.81 (3H, s), 4.65 (2H, s), 6.99 (1H, d, J 8.3 Hz), 7.43 (1H, d, J 1.5 Hz). 7.59 (1H, dd, J 8.5, 1.9 Hz), 11.10 (1H, br s). LCMS (ES+) 208 (M+H)+.

Sources & evidence

ORD record
ord-d8e662b6399d4aa7ba1ab38a9902cb8c
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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