Ethyl Acetoacetate → HCID 178472845, compound

HRID 59624

Reaction equation

HRID 59624 reaction equation
Cl.[Br:2][C:3]1[C:4]([O:10][CH3:11])=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[N:12]([O-])=O.[Na+].[CH2:16]([O:18][C:19](=[O:24])[CH2:20][C:21]([CH3:23])=[O:22])[CH3:17].C(=O)(O)[O-].[Na+]>Cl.CO>[Br:2][C:3]1[C:4]([O:10][CH3:11])=[C:5]([NH:6][N:12]=[C:20]([C:21](=[O:22])[CH3:23])[C:19]([O:18][CH2:16][CH3:17])=[O:24])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 868104143-Bromo-2-Methoxyaniline hydrochloride

Product 1

HCID 178472845HCID 178472845, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-2-methoxyaniline hydrochloride (10 g) prepared as in Example 15, in hydrochloric acid (13.5 mL of concentrated hydrochloric acid in 136.5 mL of water) was added a solution of sodium nitrite (3.47 g in 10 mL of water) at about −5° C. to about 5° C. under stirring. The reaction mixture was stirred for about 1 hour at about −5° C. to about 5° C. Then ethylacetoacetate (6.55 g) was added to the reaction mixture and stirred for about 3 hours at about −5° C. to about 5° C. Sodium bicarbonate and methanol was then added to the reaction mixture. The reaction mixture was stirred at about −5° C. to about 5° C. for about 1 hour. The mixture was filtered to give a solid, which was washed with water and dried at about 50° C. to about 55° C. Yield: 13.3 g

Workup

  1. stirringThe reaction mixture was stirred for about 1 hour at about −5° C. to about 5° C
  2. stirringstirred for about 3 hours at about −5° C. to about 5° C
  3. stirringThe reaction mixture was stirred at about −5° C. to about 5° C. for about 1 hour
  4. filtrationThe mixture was filtered
  5. customto give a solid, which
  6. washwas washed with water
  7. customdried at about 50° C. to about 55° C

Sources & evidence

ORD record
ord-e250670b322b43899edd2e2071c6b71d
Source dataset
uspto-grants-2016_09
Patent number
US09440927B2

Linked notes

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