alpha-Chloro-m-nitrotoluene → HCID 53991787, compound

HRID 1459619Notes

Reaction equation

[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[N+:24]([C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Cl)([O-:26])=[O:25].[K+].[Br-]>>[OH:1][CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[N:15]([CH2:30][C:29]2[CH:32]=[CH:33][CH:34]=[C:27]([N+:24]([O-:26])=[O:25])[CH:28]=2)[C:14]2[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:13]=2[O:12]1

Participants

Reactant 3

HCID 12078alpha-Chloro-m-nitrotoluene

HCID 253877Potassium Bromide

HCID 53805698HCID 53805698, compound

Product 1

HCID 53991787HCID 53991787, compoundYield 30%

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-7-methoxy-3-oxo-2H-1,4-benzoxazine by methods F and I, alkylating with 3-nitrobenzyl chloride, in 30% yield, mp 116°-118° C.; MS (Cl) MH+ 359; IR (KBr) 3306, 3086, 2926, 2872, 1628, 1595, 1476, 1309, 1290, 1255, 1087, 999, 713, 458 cm-1 ; 1H NMR (DMSO-d6) δ 8.14 (s, 1H), 8.11 (s, 1H), 7.63 (m, 2H), 6.97 (d, 1H, J=8.93 Hz), 6.66 (d, 1H, J=2.42 Hz), 6.53 (d, 1H, J=8.87 Hz), 5.26 (s, 2H), 4.87 (dd, 1H, J=8.98, 3.78 Hz), 4.72 (t, 1H, J=5.23 Hz), 3.68 (s, 3H), 3.61 (m, 2H), 2.01 (m, 1H), 1.90 (m, 1H). Anal. Calc'd for C18H18N2O6 : C 60.33 H 5.06, N 7.82. Found: C 59.96, H 5.08, N 7.62.

Sources & evidence

ORD record: ord-8bec106881c5403498ff0e32c395e44d
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854242

Reaction notes

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