Ammonium Acetate → HCID 178500060, compound

HRID 620754Notes

Reaction equation

HRID 620754 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:4]=1[CH:13]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:14](OC)=[O:15])=O.C([O-])(=O)C.[NH4+:28]>C(O)(=O)C>[C:20]([CH2:19][CH2:18][C:13]1[C:4]2[C:3](=[CH:8][C:7]([O:9][CH3:10])=[C:6]([O:11][CH3:12])[CH:5]=2)[CH:1]=[N:28][C:14]=1[OH:15])([O:22][CH3:23])=[O:21]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 14626123HCID 14626123, compound

Product 1

HCID 178500060HCID 178500060, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 8.34 grams of dimethyl 2-(2-formyl-4,5-dimethoxyphenyl)glutarate (25.74 mmol) (which is the product of Example 8e(1)), 17.86 grams anhydrous ammonium acetate (232 mmol) and 15 ml glacial acetic acid was heated to 75° C. and was maintained at that temperature for 30 minutes. After cooling, the yellow precipitate was isolated by filtration, washed with water and dried to provide 5.78 grams of Compound Q (77% yield). Recrystallization from methanol and trituration with ether (to remove any trace amounts of methanol) provided 4.57 grams of pure Compound Q having a melting point of 178° to 180° C.

Workup

  1. temperaturewas maintained at that temperature for 30 minutes
  2. temperatureAfter cooling
  3. customthe yellow precipitate was isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-91392324e91a4d9291a4a0aef83e1d98
Source dataset
uspto-grants-1989_04
Patent number
US04822800

Reaction notes

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