Benzyl Alcohol → HCID 54198235, compound

HRID 844032Notes

Reaction equation

HRID 844032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[N:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])[CH:5]=[N:6][CH:7]=1.[CH2:18](O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC.C(OCC)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:18]([O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[N:17][C:9]=1[O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 3283Diethyl EtherHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22612082HCID 22612082, compound

Product 1

HCID 54198235HCID 54198235, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A 15 ml flask was charged with 2-(5-chloro-pyridin-3-yloxy)-nicotinic acid (0.056 grams, 0.22 mmole), benzyl alcohol (0.052 grams, 0.44 mmole), 4-DMAP (˜3 mg), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (0.048 grams, 0.25 mmole), diethyl ether (4 ml) and pyridine (1 ml) and stirred at room temperature. After 1 hour the mixture was concentrated under reduced pressure and purified by column chromatography on silica gel eluting with 9/1 ethyl acetate/hexane to give 0.060 g of the title compound as a colorless oil. Anal. calcd. for C18H13ClN2O3: M.S. m/z [M+] 341; 1H NMR (CD3OD) d 4.58 (s, 2H), 7.45(m, 7H), 7.71 (s, 1H), 8.28 (m, 2H), 8.38 (m, 2H).

Workup

  1. concentrationAfter 1 hour the mixture was concentrated under reduced pressure
  2. custompurified by column chromatography on silica gel eluting with 9/1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-0f005fa3cd8548cbba2d256e49213a46
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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