Hydrochloric Acid → 3-({4-[(4-Acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-phenyl}-hydroxy-methyl)-benzonitrile

HRID 1161041Notes

Reaction equation

HRID 1161041 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([O:27]C3CCCCO3)[C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[C:22]#[N:23])=[CH:14][CH:13]=2)=[C:6]([CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2].Cl>CO>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([OH:27])[C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[C:22]#[N:23])=[CH:16][CH:17]=2)=[C:6]([CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666995503-[{4-[(4-Acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-phenyl}-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

Product 1

HCID 666995203-({4-[(4-Acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-phenyl}-hydroxy-methyl)-benzonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-[{4-[(4-acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-phenyl}-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (538 mg, 1.1 mmol) in MeOH (5 mL) is added conc. HCl (0.33 mL). The reaction mixture is stirred at RT for 6 h. The reaction mixture is concentrated and the residue partitioned between saturated aqueous NaHCO3 and EtOAc. The organic layer is separated and the aqueous extracted with EtOAc (2×). The organic layers are combined, washed with brine, dried over Na2SO4, and concentrated. The residue is purified by flash column chromatography using 40% EtOAc/hexane as eluent. Obtained is the title compound as yellow foam (305 mg, 72%). LC-MS (m/e): 385 (M−1).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue partitioned between saturated aqueous NaHCO3 and EtOAc
  3. customThe organic layer is separated
  4. extractionthe aqueous extracted with EtOAc (2×)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash column chromatography
  9. customObtained

Sources & evidence

ORD record
ord-fedd8d182e034c9d96ad3a71232c186c
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

Loading…