Ethyl Acetoacetate → HCID 178472848, compound

HRID 59616

Reaction equation

HRID 59616 reaction equation
[NH2:1][C:2]1[C:3]([O:17][CH3:18])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:19]([O-])=O.[Na+].[C:23]([O:29][CH2:30][CH3:31])(=[O:28])[CH2:24][C:25]([CH3:27])=[O:26].C(=O)(O)[O-].[Na+]>Cl.C(O)C.CO>[CH2:30]([O:29][C:23]([C:24](=[N:19][NH:1][C:2]1[C:3]([O:17][CH3:18])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1)[C:25](=[O:26])[CH3:27])=[O:28])[CH3:31]

Participants

8

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 57483786[1,1'-Biphenyl]-3-carboxylic acid, 3'-amino-2'-methoxy-

Product 1

HCID 178472848HCID 178472848, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 3′-amino-2′-methoxybiphenyl-3-carboxylic acid (5 g) prepared as in Example 6, in hydrochloric acid (8.5 mL) and methanol (90 mL) was added a solution of sodium nitrite (1.41 g in 400 mL of water) at about 0° C. to about 5° C. under stirring. The reaction mixture was stirred for about 15 minutes at about 5° C. Then ethyl acetoacetate (2.7 g) was added and the reaction mixture was stirred for about 15 minutes at about 0° C. to about 5° C. Solid sodium bicarbonate (15 g) and ethanol (30 mL) was added and the reaction mixture was allowed to warm to about room temperature and stirred for about 2 hours. The mixture was filtered, washed with water (50 mL) and dried under vacuum at about 35° C. to about 40° C. for about 6 hours.

Workup

  1. stirringThe reaction mixture was stirred for about 15 minutes at about 5° C
  2. stirringthe reaction mixture was stirred for about 15 minutes at about 0° C. to about 5° C
  3. temperatureto warm to about room temperature
  4. stirringstirred for about 2 hours
  5. filtrationThe mixture was filtered
  6. washwashed with water (50 mL)
  7. customdried under vacuum at about 35° C. to about 40° C. for about 6 hours

Sources & evidence

ORD record
ord-122bb4bae9464a4a9d01a270231344af
Source dataset
uspto-grants-2016_09
Patent number
US09440927B2

Linked notes

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