Formic Acid → HCID 178500540, compound

HRID 1766193Notes

Reaction equation

HRID 1766193 reaction equation
O(Cl)Cl.[P+3].O.[NH2:6][C:7]1[CH:8]=[C:9]([C:14](=[O:21])[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:10]=[CH:11][C:12]=1[NH2:13].[K+].[Br-].[CH:24](O)=O>>[NH:13]1[C:12]2[CH:11]=[CH:10][C:9]([C:14](=[O:21])[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:8][C:7]=2[N:6]=[CH:24]1

Participants

6

Reactant 5

HCID 284Formic AcidHCID 962WaterHCID 253877Potassium BromideHCID 21109927HCID 21109927, compoundHCID 178479710HCID 178479710, compound

Product 1

HCID 178500540HCID 178500540, compound

Conditions

Temperature
60 °C

Procedure

75 ml of phosphorus(III)oxychloride were slowly added dropwise, while cooling externally with water, to a solution of 20.0 g (0.09 mol) of methyl 4-(3,4-diaminophenyl)-4-oxobutanoate in 50 ml of formic acid and the mixture was then stirred for another 40 minutes at a reaction temperature of 60° C. It was left to cool, then the mixture was stirred into 500 g of crushed ice while cooling externally with ice and made weakly ammoniacal. It was then extracted exhaustively with ethyl acetate, the combined extracts were dried over magnesium sulphate and concentrated by evaporation in vacuo. 8.29 g (40% of theoretical) of a colourless, crystalline substance were obtained. IR (KBr): 1732.0, 1679.9 cm−1 (C═O)

Workup

  1. waitIt was left
  2. temperatureto cool
  3. temperaturewhile cooling externally with ice
  4. extractionIt was then extracted exhaustively with ethyl acetate
  5. dry with materialthe combined extracts were dried over magnesium sulphate
  6. concentrationconcentrated by evaporation in vacuo
  7. custom8.29 g (40% of theoretical) of a colourless, crystalline substance were obtained

Sources & evidence

ORD record
ord-6b9ebee5c5b34ad6b73d9cffc63ef426
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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