1-Chloromethylnaphthalene → HCID 53861434, compound

HRID 1459624Notes

Reaction equation

HRID 1459624 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.Cl[CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1.[K+].[Br-]>>[OH:1][CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[N:15]([CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1

Participants

4

Reactant 3

HCID 68451-ChloromethylnaphthaleneHCID 253877Potassium BromideHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 53861434HCID 53861434, compound

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 1-chloromethylnaphthalene, in 42% overall yield. The crude product was crystallized from ether/EtOAc/hexane to afford a white solid, mp 100°-104° C.; IR (KBr) 3435, 2896, 1668, 1504, 1414, 1253, 1132, 1068, 768, 758 cm-1 ; 1H NMR (CDCl3) δ 1.92 (br s, 1H Plus HDO), 2.26-2.44 (m, 2H), 3.96 (t, J=5.6 Hz, 2H), 4.94 (dd, J=7.5, 5.6 Hz, 1H), 5.62 (ABq, JAB =16.9 Hz, 2H), 6.72 (dd, J=8.0, 1.1 Hz, 1H), 6.84 (td, J=8.1, 1.5 Hz, 1H), 6.96-7.11 (m, 3H), 7.36 (t, J=7.4 Hz, 1H), 7.54-7.64 (m, 2H), 7.78 (d, J=8.2 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 8.04 (d, J=8.1 Hz, 1H); MH+ at m/z=334; Anal. Calc'd for C21H19NO3 : C, 75.66; H, 5.74; N, 4.20. Found: C, 75.56; H, 5.80; N, 4.14.

Workup

  1. customThe crude product was crystallized from ether/EtOAc/hexane
  2. customto afford a white solid, mp 100°-104° C.

Sources & evidence

ORD record
ord-92695d69427247b4917ddf0920a24415
Source dataset
uspto-grants-1998_12
Patent number
US05854242

Reaction notes

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