Sodium hydride → HCID 69017886, compound

HRID 491607Notes

Reaction equation

HRID 491607 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:11])=[C:8]([OH:10])[CH:9]=1.Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C=O)C>[Cl:11][C:7]1[CH:6]=[CH:5][C:4]([NH2:3])=[CH:9][C:8]=1[O:10][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 806765-Amino-2-chlorophenolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 69017886HCID 69017886, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring RT slurry of NaH (0.10 g of a 60% by weight oil dispersion, 2.5 mmol) in DMF (2 mL) was added 5-amino-2-chlorophenol (0.20 g, 1.4 mmol). The mixture was stirred for 10 min before adding 1-(2-chloroethyl-pyrrolidine hydrochloride (0.17 g, 1.0 mmol). The reaction was heated at 80° C. for 15 h. The reaction was quenched with water, treated with 1N NaOH, and extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel chromatography to yield title compound. MS: (MH+)=241.2; Calc'd 240.74 for C12H17ClN2O.

Workup

  1. customThe reaction was quenched with water
  2. additiontreated with 1N NaOH
  3. extractionextracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8096cc2a3b3c4e24840ff492de607572
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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