Hydrochloric Acid → HCID 178500931, compound

HRID 241806

Reaction equation

HRID 241806 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:9]([O-])=O.[Na+].[CH3:13][O:14][C:15]([CH2:17][C:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:19])=[O:16].[C:25]([O-:28])(=O)C.[Na+].[CH2:30]([OH:32])C>O>[CH3:24][O:23][C:21](=[O:22])[C:20](=[N:9][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:32][CH3:30])=[C:5]([O:28][CH3:25])[CH:4]=1)[C:18](=[O:19])[CH2:17][C:15]([O:14][CH3:13])=[O:16]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6115AnilineHCID 74591Dimethyl 3-oxoglutarateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178500931HCID 178500931, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A mixture of 2.5 ml of concentrated HCl, 5 ml of H2O, and 5.523 mmoles of aniline (26) was treated with a solution of sodium nitrite 381 mg (5.52 mmoles) in 5 ml of water in an ice bath. This reaction was stirred for two hours to give crude diazonium chloride (27) which was not isolated. The crude diazonium salt solution was poured into a mixture of 961 mg of dimethyl acetonedicarboxylate (2) in 3 ml of ethanol and 3 g of sodium acetate in 10 ml of water with vigorous stirring. Product precipitated immediately. The reaction was allowed to stir for an additional 2 hours, then filtered and dried to give 1.363 g of the desired hydrazone (28) as a solid. MS+: m/e=339.1 (M+H).

Workup

  1. customto give crude diazonium chloride (27) which
  2. customwas not isolated
  3. customProduct precipitated immediately
  4. stirringto stir for an additional 2 hours
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-6ef0804db229450ca0083845d6e32db9
Source dataset
uspto-grants-2014_02
Patent number
US08653088B2

Linked notes

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