8-Bromo-3,4-dihydro-2H-1,4-benzoxazine → 1-(8-Bromo-2H-benzo[b][1,4]oxazin-4(3H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

HRID 2175219Notes

Reaction equation

HRID 2175219 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1C[CH2:5][CH2:6][N:7]2[C:12](=[O:25])[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[CH3:24].BrC1C2[O:33]CCNC=2C=CC=1>>[Br:1][C:2]1[C:3]2[O:33][CH2:5][CH2:6][N:7]([C:12](=[O:25])[CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=3[CH3:24])[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 162444528-Bromo-3,4-dihydro-2H-1,4-benzoxazineHCID 709817961-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

Product 1

HCID 709826601-(8-Bromo-2H-benzo[b][1,4]oxazin-4(3H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

Procedure

The title compound was prepared using a procedure analogous to 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one except that 5-bromo-1,2,3,4-tetrahydroquinoline, HCl salt was replaced by 8-bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine. LCMS, [M+H]+=404.1. 1H NMR (400 MHz, CDCl3) δ 7.33 (d, J=8.0 Hz, 1H), 7.26-7.21 (m, 1H), 7.00 (t, J=8.0 Hz, 1H), 6.78-6.71 (m, 2H), 6.64 (d, J=8.1 Hz, 1H), 4.36-4.28 (m, 2H), 3.98 (t, J=5.8 Hz, 2H), 3.95-3.90 (m, 2H), 2.80 (t, J=7.2 Hz, 2H), 2.24 (s, 3H), 2.19 (dt, J=13.1, 6.4 Hz, 2H), 2.02 (s, 3H).

Sources & evidence

ORD record
ord-affb1bfaea914626b8947c2330fa1fb2
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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