3-Nitrophenylboronic Acid → 6(3-Nitrophenyl)-spiro[4H-3,1-benzoxazine-4,1'-cyclohexane]-2(1H)-one

HRID 413133Notes

Reaction equation

HRID 413133 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:16][C:15](=[O:17])[O:14][C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[C:6]=2[CH:7]=1.[N+:18]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]>>[N+:18]([C:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[CH:4][C:5]3[NH:16][C:15](=[O:17])[O:14][C:8]4([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]4)[C:6]=3[CH:7]=2)[CH:24]=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 220219046-Bromospiro[4H-3,1-benzoxazine-4,1'-cyclohexan]-2(1H)-one

Product 1

HCID 99239216(3-Nitrophenyl)-spiro[4H-3,1-benzoxazine-4,1'-cyclohexane]-2(1H)-one

Procedure

Prepared from 6-bromo-spiro[4H-3,1-benzoxazine-4,1′-cyclohexane]-2(1H)-one and 3-nitrophenyl boronic acid according to Procedure A. Off-white solid: mp 245-246° C. 1H-NMR (CDCl3) δ8.39 (t, 1H, J=1.9 Hz), 8.20 (dd, 1H, J=8.2, 1.4 Hz), 8.11 (s, 1H, D2O exchangeable), 7.86 (d, 1H, J=8.0 Hz), 7.62 (t, 1H, J=8.1 Hz), 7.50 (dd, 1H, J=8.2, 1.9 Hz), 7.39 (d, 1H, J=1.8 Hz), 6.93 (d, 1H, J=8.2 Hz), 2.25 (d, 2H, J=12.7 Hz), 1.60-1.99 (m, 7H), 1.31-1.42 (m, 1H); MS (EI) m/z 337 ([M−H]−, 100%). Anal. Calc. For C19H18N2O4.0.35H2O: C, 66.21, H, 5.47, N, 8.13. Found: C, 66.22, H, 5.43, N, 7.86.

Sources & evidence

ORD record
ord-7c1e82afda0344778e9745b6af154d36
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

Loading…