5-Chloro-2-nitrobenzoic acid → HCID 45444158, compound

HRID 655706Notes

Reaction equation

HRID 655706 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10](Cl)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].[CH2:14]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)(=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:24]2[CH2:25][CH2:26][N:21]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:22][CH2:23]2)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 172865-Chloro-2-nitrobenzoic acidHCID 759941-Benzylpiperazine

Product 1

HCID 45444158HCID 45444158, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 20 g of 2-nitro-5-chlorobenzoic acid and 50 mL of N-benzylpiperazine is stirred at 120° C. for 6 hours. To the reaction mixture 250 mL of ethyl acetate is added. The precipitated yellow crystalline material is filtered off, dissolved in 200 mL of water. The pH of the mixture is adjusted to 6 with acetic acid. The precipitated material is filtered off, washed with water and dried, to obtain 30 g of the title compound. M.p.: 172° C.

Workup

  1. filtrationThe precipitated yellow crystalline material is filtered off
  2. dissolutiondissolved in 200 mL of water
  3. filtrationThe precipitated material is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-555619a41a224fdab6c40d5a4b71f585
Source dataset
uspto-grants-2011_12
Patent number
US08071601B2

Reaction notes

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