Potassium Bromide → 3,3'-Dihydroxy-2,2'-biquinoline

HRID 258405Notes

Reaction equation

HRID 258405 reaction equation
[K+].[Br-].[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:14]1[N:15]=[CH:16][C:17]2[C:22]([C:23]=1[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=2>C(Cl)(Cl)Cl>[OH:3][C:4]1[C:5]([C:14]2[C:23]([OH:24])=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 1357498164,4'-Dihydroxy-3,3'-biisoquinoline

Product 1

HCID 1357374843,3'-Dihydroxy-2,2'-biquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Yield 0.17 g 94.4%)--melting point>360° C.--RF (silica gel/i-propanol)=0.82.--IR (KBr): 3420 cm-1 (m), 3067-2550 (m, OH), 1574 (m), 1508 (m), 1503 (m), 1466 (m), 1425 (w), 1400 (w), 1376 (m), 1332 (s), 1281 (w), 1249 (w), 1217 (s), 1161 (w), 1141 (s), 755 (s).--UV/VIS (chloroform): λmax (ε)=399 nm (9202), 328 nm (7975).--1H-NMR ((D6)DMSO/TMS): δ:6.96-7.58 (m, 6H, 5-H, 5'-H, 6-H, 6'-H, 7-H, 7'-H), 7.98 (d, J8,7 =J8',7' 8.0 Hz, 2H, 8-H, 8'-H), 8.87 (s, 2H, 4-H, 4'-H).--MS (70 eV): m/z (%)=298 (18) M+ +1, 288 (100) M+, 287 (16), 271 (7) M+ -OH, 260 (7), 259 (17), 232 (5), 231 (9), 204 (7), 176 (s), 88 (4).

Sources & evidence

ORD record
ord-ddf068b11ec54b7eabda44d9fa876c42
Source dataset
uspto-grants-1993_11
Patent number
US05266700

Reaction notes

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