Quinolinium, 1-ethyl-, iodide (1:1) → HCID 19877862, compound

HRID 1885363Notes

Reaction equation

HRID 1885363 reaction equation
[I-].[CH2:2]([N+:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:3].[C:14]1([B-:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+]>O>[C:33]1([B-:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1.[CH2:2]([N+:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 69446Quinolinium, 1-ethyl-, iodide (1:1)HCID 2723787Sodium Tetraphenylborate

Product 1

HCID 19877862HCID 19877862, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 28.5 g (0.10 mol) of N-ethylquinolinium iodide in 300 mL of water was added to a solution of 34.2 g (0.10 mol) of sodium tetraphenylborate in 350 mL of water. A precipitate immediately formed. The mixture was stirred 30 minutes and was then filtered. The solid was washed with water and methanol and recrystallized from acetonitrile. The solid was collected and dried to give 27.2 g (57.0%) of product; mp=215°-218° C. 1H NMR was consistent with the proposed structure. Atomic analysis calculated for C35H32BN (477.46): 88.0% C, 6.8% H, 2.3% B, 2.9% N. Found: 88.5% C, 6.8% H, 2.2% B, 2.7% N.

Workup

  1. customA precipitate immediately formed
  2. filtrationwas then filtered
  3. washThe solid was washed with water and methanol
  4. customrecrystallized from acetonitrile
  5. customThe solid was collected
  6. customdried

Sources & evidence

ORD record
ord-4b5c0511e49a49b9a6c87825bd04b12c
Source dataset
uspto-grants-1992_09
Patent number
US05144036

Reaction notes

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