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Ammonium Chloride → N-(3-cyclohexylphenyl)-4-hydroxy-3-methoxyphenylacetamide

HRID 7061
Notes
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Reaction equation

HRID 7061 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](I)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20].[Br-].[CH:22]1([Zn+])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[Cl-].[NH4+]>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:22]1([C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:19][CH3:20])[CH:4]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 120966604-hydroxy-N-(3-iodophenyl)-3-methoxyphenylacetamideHCID 178418970HCID 178418970, compound

Product 1

HCID 9881043N-(3-cyclohexylphenyl)-4-hydroxy-3-methoxyphenylacetamide

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 8028TetrahydrofuranSolvent2×

Procedure

Intermediate 1 (850 mg) and tetrakis(triphenylphosphine)-palladium (0) (250 mg) are dissolved in tetrahydrofuran (16 ml), and thereto is added a 0.5 M tetrahydrofuran solution (20 ml) of cyclohexylzinc bromide under argon atmosphere at room temperature, and the mixture is stirred for 18 hours. A saturated aqueous ammonium chloride solution is added to the reaction solution, and the mixture is extracted with ethyl acetate. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (120 mg).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b59d64d91f264abeae1d4d6a9e60e2b0
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084176B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes