Hydrochloric Acid → N-hydroxy-N-(1-hydroxy-2-naphthyl)-3-methoxycarbonylbenzamide

HRID 1886263Notes

Reaction equation

HRID 1886263 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-:7])=O)[CH:3]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.Cl.[OH:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[NH:37][OH:38].C(N(CC)CC)C.Cl>C1COCC1.CCCCCC.C(OCC)(=O)C.O.C(Cl)Cl>[OH:38][N:37]([C:28]1[CH:29]=[CH:30][C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]=1[OH:26])[C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([C:1]([O:12][CH3:13])=[O:11])[CH:3]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69512791,3-Benzenedicarboxylic acid, monomethyl esterHCID 856138501-Hydroxy-2-naphthylhydroxylamine hydrochloride

Product 1

HCID 15728707N-hydroxy-N-(1-hydroxy-2-naphthyl)-3-methoxycarbonylbenzamideYield 55%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Into a 25 ml dry methylene chloride solution of 500 mg (2.78 mmol) of monomethyl isophthalate and 215 μl (2.78 mmol) of DMF was added under N2 atmosphere 546 μl (6.26 mmol) of oxalyl chloride at 0° C., and subsequently, the mixture was returned to room temperature and stirred for one hour. The mixture was added dropwise under an N2 atmosphere to a solution of 1.76 g (8.34 mmol) of 1-hydroxy-2-naphthylhydroxylamine hydrochloride, 2.9 ml (21 mmol) of triethylamine in THF (25 ml), and water (5 ml), followed by stirring as such at room temperature for one hour. The reaction was completed by an addition of 4N hydrochloric acid, and the mixture extracted with methylene chloride. The organic layer was washed with 4N hydrochloric acid, water, and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the crude product obtained was subjected to silica gel column chromatography (hexane:ethyl acetate 6:1→4:1) to give 513 mg (55%) hydroxyamic acid.

Workup

  1. customwas returned to room temperature
  2. stirringby stirring as such at room temperature for one hour
  3. extractionthe mixture extracted with methylene chloride
  4. washThe organic layer was washed with 4N hydrochloric acid, water, and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. customthe crude product obtained

Sources & evidence

ORD record
ord-7a7c86fd6b594b228f9c662ddbaac9dc
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Reaction notes

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