Water → HCID 59281523, compound
Reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([Br:9])[CH:5]=[CH:4][C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19](Br)=[O:20].O>CN(C)C=O.C(OCC)(=O)C>[Br:9][C:6]1[CH:5]=[CH:4][C:3]2[O:10][CH2:18][C:19](=[O:20])[NH:1][C:2]=2[C:7]=1[CH3:8]Participants
Procedure
An ice cold suspension of 2-amino-4-bromo-3-methylphenol (3.81 g, 18.86 mmol) and potassium carbonate (10.42 g, 75 mmol) in N,N-Dimethylformamide (DMF) (25 mL) was treated by dropwise addition of bromoacetyl bromide (1.971 mL, 22.63 mmol). The mixture was warmed to ambient temperature and stirred for one hour. Water was added and the mixture was diluted with ethyl acetate. There were insoluble solids, so the entire mixture was passed through a fine glass frit to afford 6-bromo-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one as an off-white solid (1.20 g, 26%). The filtrate was extracted with ethyl acetate. The extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated to give slightly impure 6-bromo-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one as a reddish-brown solid (3.05 g, 67%): 1H NMR (400 MHz, DMSO-d6) δ ppm 10.40 (br. s., 1 H), 7.15 (d, J=8.6 Hz, 1 H), 6.79 (d, J=8.6 Hz, 1 H), 4.50 (s, 2 H), 2.30 (s, 3 H); LC/MS (m/z) ES+=242 (M+1).
Sources & evidence
- ORD record
- ord-13038b633c2a48d198fc7870b5ddeaa0
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609653B2
Reaction notes
Loading…