4-(Chloromethyl)pyridine → HCID 54484927, compound

HRID 1459616Notes

Reaction equation

HRID 1459616 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:29]=[CH:28][N: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[CH:29]=[CH:28][N: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 745714-(Chloromethyl)pyridineHCID 253877Potassium BromideHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 54484927HCID 54484927, compoundYield 12%

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and H, alkylating with 4-chloromethylpyridine, in 12% yield and isolated as a beige solid, mp 153°-154° C.; IR (KBr) 3204, 1679, 1505, 1407, 1283, 1256, 1077, 1065, 750 cm-1 ; 1H NMR (CDCl3) δ 2.18-2.38 (m, 3H), 3.93 (br q, J=3.9 Hz, 2H), 4.88 (dd, J=7.7, 5.4 Hz, 1H), 5.15 (s, 2H), 6.73 (d, J=7.6 Hz, 1H), 6.92 (td, J=6.7, 3.2 Hz, 1H), 6.98-7.06 (m, 2H), 7.15 (d, J=5.9 Hz, 2H), 8.56 (dd, J=4.5, 1.5 Hz, 2H); MH+ at m/z=285; Anal. Calc'd for C16 H16N2O3 : C, 67.59; H, 5.67; N, 9.85. Found: C, 67.67; H, 5.78; N, 9.79.

Workup

  1. customisolated as a beige solid, mp 153°-154° C.

Sources & evidence

ORD record
ord-61ce93852ee2425dbc23dbe6b2059e7f
Source dataset
uspto-grants-1998_12
Patent number
US05854242

Reaction notes

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