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Hydrochloric Acid → HCID 178418662, compound

HRID 37613
Notes
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Reaction equation

HRID 37613 reaction equation
[H-].[Na+].C(S)CC.[CH2:7]([C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[N:37](C4C=CC([N+]([O-])=O)=CC=4)[N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[CH3:8].[ClH:47]>CCCCCC.CN1CCCC1=O.O>[ClH:47].[CH2:7]([C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:25][CH:26]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7848Propyl mercaptanHCID 24758Sodium hydrideHCID 199357842-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline

Product 1

HCID 178418662HCID 178418662, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8058HexaneSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Sodium hydride (50% dispersion in mineral oil; 0.091 g; 1.9 mmol) was washed with hexane, dried with a stream of nitrogen and covered with N-methylpyrrolidone (NMP) (5 ml). The mixture was cooled to below 10° C. and propanethiol (0.145 g; 1.9 mmol) was added slowly with stirring. After 15 minutes, a solution of 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline (A) (0.5 g; 0.95 mmol) in NMP (10 ml) was added slowly maintaining the temperature of the reaction mixture below 10° C. The mixture was then stirred for 2 hours. Concentrated hydrochloric acid was added until the reaction mixture was pH2. Water (25 ml) was then added and the suspended white solid collected by filtration. The crude product was recrystallised from ethanol to give 2-ethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline hydrochloride as a solid, in 64% yield; m.p. 178°-181° C.; NMR (d6 -DMSO): 1.53(3H, t), 3.30(2H, q), 5.65(2H, s), 7.25(2H, d), 7.50-7.75(6H, m), 7.80(1H, t), 7.90(1H, s), 8.00(1H, t), 8.35(1H, d), 8.50(1H, d).

Workup

  1. customdried with a stream of nitrogen
  2. temperatureThe mixture was cooled to below 10° C.
  3. temperaturemaintaining the temperature of the reaction mixture below 10° C
  4. stirringThe mixture was then stirred for 2 hours
  5. filtrationthe suspended white solid collected by filtration
  6. customThe crude product was recrystallised from ethanol

Sources & evidence

ORD record
ord-e87f45f169df444b935b6b0d7d41c90c
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05420292

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes