Methane → HCID 15078769, compound

HRID 1651426Notes

Reaction equation

HRID 1651426 reaction equation
O[C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[OH:8].[C:9]1([CH3:15])[CH:14]=[CH:13]C=CC=1.[NH2:16][CH2:17][CH2:18][CH2:19][OH:20].C>C(O)CCC.O>[CH2:15]([O:8][C:3]1[C:4](=[O:7])[C:5](=[O:6])[C:2]=1[NH:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:9][CH2:14][CH3:13]

Participants

7

Reactant 4

HCID 297MethaneHCID 1140TolueneHCID 90863-Amino-1-propanolHCID 17913Squaric acid

Product 1

HCID 15078769HCID 15078769, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A slurry of 1,2-dihydroxy-1-cyclobutene-3,4-dione (15.0 g, 131.5 mmol), 45 mL of 1-butanol and 30 mL of toluene was heated at reflux under a nitrogen atmosphere with stirring under a Dean-Stark Water separator until water stopped passing over. The reaction mixture was then cooled to 0° C. and a solution of 3-amino-1-propanol (9.88 g, 131.5 mmol) in 10 mL of 1-butanol was added dropwise. After 1 hour at ambient temperature, charcoal was added and the mixture filtered through a pad of diatomaceous earth. The filtrate was evaporated under reduced pressure to give 28.9 g of the title compound as an oil. A portion of the product (24.7 g) was dissolved in dichloromethane and filtered through a pad of about 200 g of silica gel. The pad was washed with 1.6 L of dichloromethane:methanol (9:1), and the filtrate was evaporated in vacuo to produce 22.7 g of the title compound.

Workup

  1. temperatureat reflux under a nitrogen atmosphere
  2. filtrationthe mixture filtered through a pad of diatomaceous earth
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-40fffda4d70f43d78e265b80b3c013b3
Source dataset
uspto-grants-1990_05
Patent number
US04927970

Reaction notes

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