Methyl 2-chloro-5-nitrobenzoate → HCID 68982294, compound

HRID 1820859Notes

Reaction equation

HRID 1820859 reaction equation
[N:1]1([CH2:6][CH2:7][OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Na].Cl[C:11]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:16][O:15][C:13]([C:12]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:11]=1[O:8][CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:14]

Participants

6

Reactant 3

HCID 22754Methyl 2-chloro-5-nitrobenzoateHCID 762881-PyrrolidineethanolHCID 5360545Sodium

Product 1

HCID 68982294HCID 68982294, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

3.43 g (29.8 mmol) of 2-pyrrolidin-1-ylethanol is dissolved in 60 mL of toluene and 575 mg (25.0 mmol) of sodium is added batchwise. The mixture is heated to 100° C. and then stirred for a further 12 hours at 50° C. After cooling, 5.00 g (22.5 mmol) of methyl 2-chloro-5-nitrobenzoate are added batchwise and the mixture is stirred for 1 day at ambient temperature. After this time, the solvent is eliminated, the residue is taken up in methylene chloride and washed with water. The organic phase is dried over sodium sulfate and concentrated by rotary evaporation. Finally the product is purified through a silica gel column with a gradient of methylene chloride/methanol/ammonia (8:2 to 8:2:0.1) as eluant. Yield: 1.65 g (25% of theory); Rf value: 0.45 (silica gel, methylene chloride/methanol/ammonia=9:1:0.1); C14H18N2O5; EII mass spectrum: m/z=295 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture is stirred for 1 day at ambient temperature
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated by rotary evaporation
  6. customFinally the product is purified through a silica gel column with a gradient of methylene chloride/methanol/ammonia (8:2 to 8:2:0.1) as eluant

Sources & evidence

ORD record
ord-87c73b9706c34beab363fca47d1c6a16
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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