Arsenic Acid → 6-[4-(7-Phenyl-1,10-phenanthrolin-4-yl)phenyl]hexan-1-ol

HRID 432546Notes

Reaction equation

HRID 432546 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:8][CH:7]=1)=O.NC1C=CC=C2C=1N=CC=C2C1C=CC=CC=1.[As](=O)(O)(O)O.[N+:41]([C:44]1[CH:45]=[CH:46][CH:47]=[C:48]2[C:53]=1[N:52]=[CH:51][CH:50]=[C:49]2[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([O-])=O>P(=O)(O)(O)O>[C:54]1([C:49]2[C:48]3[C:53]([N:52]=[CH:51][CH:50]=2)=[C:44]2[C:45]([C:4]([C:6]4[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:8][CH:7]=4)=[CH:3][CH:2]=[N:41]2)=[CH:46][CH:47]=3)[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 234Arsenic AcidHCID 1087268-Quinolinamine, 4-phenyl-HCID 1176348-Nitro-4-phenylquinolineHCID 187596053-Chloro-1-[4-(6-hydroxyhexyl)phenyl]propan-1-one

Product 1

HCID 187596006-[4-(7-Phenyl-1,10-phenanthrolin-4-yl)phenyl]hexan-1-ol

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

The procedure followed was similar to that of Case and Strohm (Case, F. H.; Strohm, P. F. J. Org. Chem, 1962, 27, 1641-1643). 3-Chloro-1-[4-(6-hydroxyhexyl)phenyl]propan-1-one (0.73 g), 8-amino-4-phenylquinoline (0.27 g), arsenic acid (0.99 g) and 85% phosphoric acid (10 mL) were reacted as described in the procedure for the synthesis of 8-nitro-4-phenylquinoline. However during precipitation of the crude product, a pH of 6-8 was maintained in order to ensure that the alcohol functionality remained protonated. The crude product was re-crystallized with a 50:50 mixture of petroleum ether and chloroform. Further purification of the desired product was achieved using preparatory TLC with 2% methanol and 98% chloroform.

Workup

  1. customHowever during precipitation of the crude product
  2. temperaturea pH of 6-8 was maintained in order
  3. customThe crude product was re-crystallized with a 50:50 mixture of petroleum ether and chloroform
  4. customFurther purification of the desired product

Sources & evidence

ORD record
ord-4e24a1ff8ca949b3a2dc0c7d141a66b3
Source dataset
uspto-grants-2003_12
Patent number
US06664111B2

Reaction notes

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