Methyl 2-(4-aminophenyl)acetate → HCID 90109834, compound

HRID 1508689Notes

Reaction equation

HRID 1508689 reaction equation
Cl.Cl[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[N:6]=[C:5]([CH3:16])[C:4]=1[CH2:17][CH3:18].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=1>>[Cl:15][C:11]1[CH:10]=[C:9]([C:7]2[N:6]=[C:5]([CH3:16])[C:4]([CH2:17][CH3:18])=[C:3]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:25]=3)[CH:8]=2)[CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 2761030Methyl 2-(4-aminophenyl)acetateHCID 118037279HCID 118037279, compound

Product 1

HCID 90109834HCID 90109834, compoundYield 41%

Conditions

Temperature
150 °C

Procedure

An 18-mL test tube was charged with 4-Chloro-6-(3-chlorophenyl)-3-ethyl-2-methyl-pyridine HCl salt (15 mg, 0.05 mmol, 1 eq.) and methyl 2-(4-aminophenyl)acetate (20 mg, 0.12 mmol, 2.4 eq.). The resulting mixture was heated at 150° C. under Ar for 1 hr. After cooling to room temperature, the mixture was partitioned between NaHCO3 aq. (10 ml) and dichloromethane (10 ml). The organic layer was collected and concentrated on a rotary evaporator. The residue was purified by chromatography on silica gel using dichloromethane/ethyl acetate (9:1 then 3:1) as eluent to methyl 2-[4-[[6-(3-chlorophenyl)-3-ethyl-2-methyl-4-pyridyl]amino]phenyl]acetate (8 mg, 41% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between NaHCO3 aq. (10 ml) and dichloromethane (10 ml)
  3. customThe organic layer was collected
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8670be21144646889194940f5bc14387
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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