Methyl 2-[4-(aminomethyl)phenoxy]-2-(2-chlorophenyl)acetate → HCID 19781890, compound

HRID 257846Notes

Reaction equation

HRID 257846 reaction equation
[C:1]([NH:6][N:7]=[C:8](OCC)[CH2:9][CH2:10][CH2:11][CH3:12])([O:3]CC)=O.[NH2:16][CH2:17][C:18]1[CH:36]=[CH:35][C:21]([O:22][CH:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=1>C(O)C>[CH2:9]([C:8]1[N:16]([CH2:17][C:18]2[CH:36]=[CH:35][C:21]([O:22][CH:23]([C:24]([O:26][CH3:27])=[O:25])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])=[CH:20][CH:19]=2)[C:1](=[O:3])[NH:6][N:7]=1)[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 19781920Methyl 2-[4-(aminomethyl)phenoxy]-2-(2-chlorophenyl)acetateHCID 53752329Ethyl valerate carbethoxyhydrazone

Product 1

HCID 19781890HCID 19781890, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of approximately equimolar quantities of ethyl valerimidate carbethoxyhydrazone (from Step A) and methyl 2-[4-(aminomethyl)phenoxy]-2-(2-chlorophenyl)acetate (Step F) in ethanol is stirred at 80° C. under N2. After about 2 hours, or when TLC indicates complete reaction, the mixture is cooled and concentrated to dryness. The residue is re-concentrated from CH2Cl2 and then chromatographed on silica gel to yield the title compound.

Workup

  1. customreaction
  2. temperaturethe mixture is cooled
  3. concentrationconcentrated to dryness
  4. concentrationThe residue is re-concentrated from CH2Cl2
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-5d3831f9bee3421ca572860631ca2b71
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

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