Hydrochloric Acid → 473927-63-8

HRID 353064Notes

Reaction equation

HRID 353064 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N:10]([O-])=O.[Na+].[CH2:14]([O:16][C:17](=[O:23])[CH2:18]C(CCl)=O)[CH3:15].C([O-])(=O)C.[Na+].[ClH:29]>O.C(O)C>[Cl:29]/[C:18](=[N:10]\[NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)/[C:17]([O:16][CH2:14][CH3:15])=[O:23]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 69484Ethyl 4-chloroacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 12218955473927-63-8

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
-5 °C

Procedure

To p-anisidine (16 g, 0.129 mol) in conc. HCl (40 mL) and 100 mL H2O, cooled to −5° C., was added sodium nitrite (9.4 g, 0.136 mol) in H2O (60 mL). The reaction mixture was stirred at −5° C. for 20 min and a mixture of ethylchloroacetoacetate (22 g, 0.133 mol), ethanol (100 mL), sodiumacetate (32 g, 0.389 mmol), and H2O (400 mL) was added. The reaction was allowed to warm up to room temperature and stirred for 2 h. The product precipitated as a black solid. It was filtered and dried (30 g). 1H NMR (CDCl3) δ: 8.28 (s, 1H), 7.18 (d, 2H), 6.90 (d, 2H), 4.41 (q, 2H), 3.80 (s, 3H), 1.42 (t, 3H) ppm.

Workup

  1. additionwas added
  2. temperatureto warm up to room temperature
  3. stirringstirred for 2 h
  4. customThe product precipitated as a black solid
  5. filtrationIt was filtered
  6. customdried (30 g)

Sources & evidence

ORD record
ord-31600f9d1454495ab00536d112b850c1
Source dataset
uspto-grants-2004_06
Patent number
US06750225B2

Reaction notes

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