(4-Nitrophenyl)acetic acid → HCID 3522175, compound

HRID 1925386Notes

Reaction equation

HRID 1925386 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(Cl)Cl>C1COCC1.CN(C=O)C>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 531671-Methylpiperazine

Product 1

HCID 3522175HCID 3522175, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrophenylacetic acid (2.00 g, 0.011 mol) was dissolved in anhydrous THF (20 mL) with gradual addition of thionyl chloride (1.03 mL, 0.0143 mol) and a catalytic amount of DMF (2 drops) at RT and stirred for 24 h. On completion, the reaction was quenched in situ with N-methylpiperazine (3.85 g, 0.038 mol) added dropwise in a solution of DCM (20 mL) at RT and stirred overnight to give a beige suspension. The solvent was removed in vacuo and the residue partitioned between DCM (30 mL) and sodium hydroxide (1N, 30 mL). The organic layer was washed twice, dried over sodium sulphate and filtered. Removal of the solvent in vacuo yielded the title compound as an amber oil, 1.50 g (solidified on standing).

Workup

  1. customto give a beige suspension
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between DCM (30 mL) and sodium hydroxide (1N, 30 mL)
  4. washThe organic layer was washed twice
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-2d03554265b34798b9c3450876cd6578
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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