4-(Chloromethyl)pyridinium chloride → 2-Pyridin-4-yl-benzoxazol-6-ol

HRID 366446Notes

Reaction equation

HRID 366446 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=1[OH:10].Cl.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.N1C=CC=CC=1C1OC2C=C(O)C=CC=2N=1>C(N(CC)CC)C>[N:16]1[CH:17]=[CH:18][C:13]([C:12]2[O:10][C:4]3[CH:5]=[C:6]([OH:7])[CH:8]=[CH:9][C:3]=3[N:2]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 745704-(Chloromethyl)pyridinium chlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 134088224-Aminobenzene-1,3-diol hydrochlorideHCID 1357979192-(Pyridin-2-yl)-1,3-benzoxazol-6-ol

Product 1

HCID 1357979222-Pyridin-4-yl-benzoxazol-6-ol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Pyridin-4-yl-benzoxazol-6-ol was prepared using 4-aminoresorcinol hydrochloride (1.5 g, 9.3 mM), isonicotinyl chloride hydrochloride (1.8 g, 10.2 mM), triethylamine (3.0 g, 30.0 mM) and pyridinium-p-toluenesulfonate (PPTS, 800 mg, 3.2 mM) were refluxed in xylenes (50 mL) for about 24 hours as described for 2-pyridin-2-yl-benzoxazol-6-ol; m.p., 139-143° C.

Workup

  1. customm.p., 139-143° C.

Sources & evidence

ORD record
ord-43f469e41c3f4c96826fad23eb7ca5e5
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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