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Hydrochloric Acid → Ammonium Hydroxide

HRID 1661563
Notes
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Reaction equation

HRID 1661563 reaction equation
[I-].[Li+].C([O:5][C:6](=[O:33])[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[C:17]([CH3:25])=[C:16]2[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:9][C:8]=1[CH3:32])C.Cl>N1C(C)=CC=CC=1C>[NH4+:15].[OH-:5].[CH3:13][C:12]1[CH:11]=[C:10]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[C:17]([CH3:25])=[C:16]2[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:9]=[C:8]([CH3:32])[C:7]=1[C:6]([OH:33])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 582156242,6-Dimethyl-4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid ethyl ester

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 582155892,6-Dimethyl-4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid

Reagents, catalysts & solvents

1
HCID 79372,6-LutidineSolvent

Procedure

To a refluxing solution of lithium iodide (0.218 g, 1.626 mmol) in 2,6-lutidine (5 mL) is added 2,6-dimethyl-4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid ethyl ester (0.176 g, 0.407 mmol). The reaction is refluxed overnight. It is cooled to room temperature, acidified to pH 1 using 1M aqueous HCl solution and extracted with dichloromethane. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by reverse phase HPLC with Xbridge Shield RP18 column and a 0.1% aqueous NH4OH in acetonitrile gradient to afford 2,6-dimethyl-4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid as a solid. 1H NMR (400 MHz, MeOD) δ ppm 2.22 (s, 6H), 2.28 (s, 3H), 5.22 (s, 2H), 6.49 (s, 2H), 7.15 (dd, J=8.6, 2.0 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.51-7.57 (m, 1H), 7.61 (d, J=1.8 Hz, 1H), 7.81 (dt, J=8.1, 2.0, 1.8 Hz, 1H), 8.58 (d, J=1.3 Hz, 1H), 8.61 (dd, J=4.9, 1.6 Hz, 1H). HRMS (ESI) m/z 405.1379 [(M+H)+ Calcd for C24H21ClN2O2: 405.1370].

Workup

  1. temperatureThe reaction is refluxed overnight
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by reverse phase HPLC with Xbridge Shield RP18 column

Sources & evidence

ORD record
ord-18dcbee143d64fdebbe1874f17a368a9
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030334B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes