2-(Chloromethyl)naphthalene → HCID 53656600, compound

HRID 1939379Notes

Reaction equation

HRID 1939379 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[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[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[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[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 756322-(Chloromethyl)naphthaleneHCID 253877Potassium BromideHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 53656600HCID 53656600, compound

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 2-chloromethyl naphthalene, in 81% overall yield. the crude product was crystallized from ether/hexane to afford a white solid, mp 81°-87° C.; IR (KBr) 3459, 2940, 1665, 1500, 1403, 1277, 1242, 1066, 746 cm-1 ; 1H NMR (CDCl3) δ2.23-2.40 (m, 3H), 3.95 (t, J=5.4 Hz, 2H), 4.90 (dd, J=7.6, 5.6 Hz, 1H), 5.32 (ABq, JAB =16.1 Hz, 2H), 6.87-7.03 (m, 4H), 7.38 (d, J=8.5 Hz, 1H), 7.43-7.48 (m, 2H), 7.67 (s, 1H), 7.75-7.84 (m, 3H); MH+ at m/z=334; Anal. Calc'd for C21H19NO3 : C, 75.66; H, 5.74; N, 4.20. Found: C, 75.65; H, 5.71; N, 4.02.

Workup

  1. customthe crude product was crystallized from ether/hexane
  2. customto afford a white solid, mp 81°-87° C.

Sources & evidence

ORD record
ord-f8f47b9d480e4f1899fc1621aaa6c9ad
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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