Methyl acetoacetate → HCID 726139, compound

HRID 255977Notes

Reaction equation

HRID 255977 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([O:16][CH3:17])(=[O:15])[CH2:11][C:12]([CH3:14])=O.[OH-:18].[NH4+:19]>CO>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:11]([C:10]([O:16][CH3:17])=[O:15])=[C:12]([CH3:14])[NH:19][C:12]([CH3:14])=[C:11]1[C:10]([O:16][CH3:17])=[O:18]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 14923Ammonium HydroxideHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 726139HCID 726139, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution containing 119 g of 2-fluorobenzaldehyde, 600 ml of methanol and 255 ml of methyl acetoacetate was added 200 ml of concentrated ammonium hydroxide whereupon an exothermic reaction ensued. The reaction mixture was stirred at ambient temperature for 30 minutes, next refluxed a few hours and then allowed to stand at room temperature overnight (about 15 hours). The yellow solid that crystallized was collected, washed with ether and dried in an oven at 50°-60° C. to yield 201 g of dimethyl 4-(2-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate, m.p. 206°-208° C. Concentration of the mother liquor yielded another 26.4 g of the product, m.p. 204°-206° C. The total yield was 74%.

Workup

  1. customwhereupon an exothermic reaction
  2. temperaturenext refluxed a few hours
  3. waitto stand at room temperature overnight
  4. custom(about 15 hours)
  5. customThe yellow solid that crystallized
  6. customwas collected
  7. washwashed with ether
  8. customdried in an oven at 50°-60° C.

Sources & evidence

ORD record
ord-01fac112aec2411fa8d8f189ed7ffffa
Source dataset
uspto-grants-1987_10
Patent number
US04699984

Reaction notes

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