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Hydrochloric Acid → Ethyl 4'-(3-aminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

HRID 253503
Notes
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Reaction equation

HRID 253503 reaction equation
O.NN.O=C1C2C(=CC=CC=2)C(=O)[N:6]1[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27][CH:26]=2)=[CH:21][C:20]=1[C:36]1[CH:45]=[CH:44][C:43]2[C:42]([CH3:47])([CH3:46])[CH2:41][CH2:40][C:39]([CH3:49])([CH3:48])[C:38]=2[CH:37]=1.O.Cl>C(O)C>[NH2:6][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:30]=2)=[CH:21][C:20]=1[C:36]1[CH:45]=[CH:44][C:43]2[C:42]([CH3:47])([CH3:46])[CH2:41][CH2:40][C:39]([CH3:48])([CH3:49])[C:38]=2[CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 66856613HCID 66856613, compound

Product 1

HCID 11340717Ethyl 4'-(3-aminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylateYield 37.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 μl of hydrazine monohydrate (2.05 mmol) are added to a solution of 650 mg (1 mmol) of ethyl 4′-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propoxy]-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate in 50 ml of ethanol. The reaction mixture is stirred overnight at reflux. The reaction is stopped by adding water and hydrochloric acid to pH 4, and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off. The residue is purified by chromatography on silica gel (eluent: 70/30 ethyl acetate/methanol). 180 mg of ethyl 4′-(3-aminopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a whitish solid (m.p.=155° C., yield=35%).

Workup

  1. temperatureat reflux
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customThe residue is purified by chromatography on silica gel (eluent: 70/30 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-504749a9433249c9970c743b15ebff89
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07872026B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes