Lithium hydroxide, monohydrate → HCID 11430022, compound

HRID 2262769Notes

Reaction equation

HRID 2262769 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:31])[C:18]2[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=2[O:27]C(=O)C)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.O[Li].O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:31])[C:18]2[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=2[OH:27])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67043385HCID 67043385, compound

Product 1

HCID 11430022HCID 11430022, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[3-Chloro-4-(4-chloro-phenylamino)-phenyl]-2-acetoxy-5-nitro-benzamide (155 mg) was dissolved in a 1:1 mixture of THF and water (12 ml) and LiOH.H2O (64 mg) was added. After stirring at room temperature for 2 hours the solvents were evaporated and water was added to the residue. Filtration, acidification of the filtrate and filtration of the precipitate gave a residue which was flash-chromatographed (EtOAc; 1:3) to provide N-[3-Chloro-4-(4-chloro-phenylamino)-phenyl]-2-hydroxy-5-nitro-benzamide as a curry coloured powder (70 mg). Mp. >219° C. (dec.).

Workup

  1. additionwas added
  2. customwere evaporated
  3. additionwater was added to the residue
  4. filtrationFiltration, acidification of the filtrate and filtration of the precipitate
  5. customgave a residue which
  6. customwas flash-chromatographed (EtOAc; 1:3)

Sources & evidence

ORD record
ord-9757197c11f4406da05da8c3846c9da5
Source dataset
uspto-grants-2010_12
Patent number
US07851492B2

Reaction notes

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