1-(Bromomethyl)-3-chlorobenzene → 4-(3-Chlorobenzyl)-3,4-dihydro-2-(2-hydroxyethyl)-3-oxo-6-methoxy 2H-1,4-benzoxazine

HRID 1459607Notes

Reaction equation

HRID 1459607 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br.CCO.O.[K+].[Br-]>O>[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][N:15]1[C:14]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:13]=2[O:12][CH:11]([CH2:10][CH2:9][OH:1])[C:16]1=[O:17]

Participants

6

Reactant 4

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 253877Potassium BromideHCID 19096565Water ethanolHCID 537700802-{[tert-Butyl(dimethyl)silyl]oxy}ethyl-6-methoxy-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 545462944-(3-Chlorobenzyl)-3,4-dihydro-2-(2-hydroxyethyl)-3-oxo-6-methoxy 2H-1,4-benzoxazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-6-methoxy-3-oxo-2H-1,4-benzoxazine by methods F and G, alkylating with 3-chlorobenzyl bromide, in 80% overall yield. Isolated by crystallization from EtOH/water to afford a white powder, MS (Cl) 348 (MH+); IR (KBr) 3501, 3053, 3021, 2959, 2933, 2876, 2838, 1664, 1618, 1600, 1575, 1512, 1466, 1445, 1435, 1390, 1361, 1337, 1313, 1272, 1237, 1201, 1173, 1107, 1078, 1049, 1030 cm-1 ; 1H NMR (CDCl3) δ 7.27-7.20 (m, 3H), 7.13 (m, 1H), 6.94 (d, J=8.8 Hz, 1H), 6.52 (dd, J=9.1, 2.7 Hz, 1H), 6.41 (d, J=2.7 Hz, 1H), 5.12 (d, J=16.2 Hz, 1H), 4.79 (dd, J=8.2, 5.4 Hz, 1H), 3.92 (m, 2H), 3.68 (s, 3H), 3.39-2.16 (m, 2H), 2.17 (t, J=5.9 Hz, 1H). Anal. Calc'd for C18H18ClNO4.0.25 H2O: C 61.37, H 5.29, N 3.98. Found: C 61.35, H 5.14, N 3.95.

Workup

  1. customto afford a white powder, MS (Cl) 348 (MH+)

Sources & evidence

ORD record
ord-ab62011edf9148a4b7cfbb7ae9dec8bc
Source dataset
uspto-grants-1998_12
Patent number
US05854242

Reaction notes

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