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Hydrochloric Acid → 4''-Diethylamino-3''-ethyl-4'-(3-hydroxypropoxy)-[1,1';3',1'']terphenyl-4-carboxylic acid

HRID 1158163
Notes
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Reaction equation

HRID 1158163 reaction equation
[CH2:1]([N:3]([CH2:34][CH3:35])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29]CC)=[O:28])=[CH:23][CH:22]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:6][C:5]=1[CH2:32][CH3:33])[CH3:2].[OH-].[Na+].Cl>O1CCCC1.O>[CH2:34]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][CH:26]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:6][C:5]=1[CH2:32][CH3:33])[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11662917Ethyl 4''-diethylamino-3''-ethyl-4'-(3-hydroxypropoxy)-[1,1';3',1'']terphenyl-4-carboxylate

Product 1

HCID 115106274''-Diethylamino-3''-ethyl-4'-(3-hydroxypropoxy)-[1,1';3',1'']terphenyl-4-carboxylic acidYield 31.4%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 25 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer, are placed 270 mg (0.57 mmol) of ethyl 4″-diethylamino-3″-ethyl-4′-(3-hydroxypropoxy)-[1,1′;3′,1″]terphenyl-4-carboxylate (Example 10d) and 22 mg (5.7 mmol) of solid sodium hydroxide in 5.4 mL of tetrahydrofuran. The reaction medium is heated at the reflux temperature of the tetrahydrofuran for 5 hours. The reaction medium is concentrated under vacuum. The crude reaction product obtained is taken up in water and the pH of the medium thus obtained is adjusted to pH=4 by addition of hydrochloric acid solution in a proportion of 1 mol/L. The precipitate obtained, after stirring for 30 minutes, is purified by chromatography on silica (eluent: 40/60 heptane/ethyl acetate) to give, after evaporation of the fractions, 80 mg (yield=31%) of 4″-diethylamino-3″-ethyl-4′-(3-hydroxypropoxy)-[1,1′;3′,1″]terphenyl-4-carboxylic acid in the form of a cream-colored powder (m.p.=204° C.).

Workup

  1. customInto a 25 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer
  2. concentrationThe reaction medium is concentrated under vacuum
  3. customThe crude reaction product
  4. customobtained
  5. customthe pH of the medium thus obtained
  6. customThe precipitate obtained
  7. customis purified by chromatography on silica (eluent: 40/60 heptane/ethyl acetate)
  8. customto give

Sources & evidence

ORD record
ord-a1e9d2f5a86f4792be37ca5683fa5ceb
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07807708B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes