Ethyl bromoacetate → 4H-1,4-Benzoxazine-4-acetic acid, 6-acetyl-2,3-dihydro-3-oxo-, ethyl ester

HRID 221220Notes

Reaction equation

Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([C:11]1[CH:29]=[CH:28][C:14]2[O:15][CH2:16][C:17](=[O:27])[N:18](CCCC(OCC)=O)[C:13]=2[CH:12]=1)(=[O:10])[CH3:9]>>[C:8]([C:11]1[CH:29]=[CH:28][C:14]2[O:15][CH2:16][C:17](=[O:27])[N:18]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:13]=2[CH:12]=1)(=[O:10])[CH3:9]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 68977662HCID 68977662, compound

Product 1

HCID 561794H-1,4-Benzoxazine-4-acetic acid, 6-acetyl-2,3-dihydro-3-oxo-, ethyl ester

Procedure

The compound 23b was synthesized by reacting 22 and 6d following the same protocol described for the synthesis of compound 23a. White solid (0.47 g, 32%). 1H NMR (400 MHz, CDCl3): δ 1.30 (t, J=7.2 Hz, 3H); 2.55 (s, 3H); 4.25 (q, J=7.2 Hz, 2H); 4.70 (s, 2H); 4.74 (s, 2H); 7.05 (dd, J=1.6, 8.4 Hz, 1H); 7.41-7.42 (m, 1H); 7.60-7.63 (m, 1H).

Sources & evidence

ORD record: ord-65dcea9f379147e98ad23c8779b0e998
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207163B2

Reaction notes

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