Methylamine → HCID 15924245, compound

HRID 974232Notes

Reaction equation

HRID 974232 reaction equation
[CH3:1][C:2]1[C:11]2[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=2[O:5][C:4](=O)[CH:3]=1.[CH3:14][NH2:15]>CO>[CH3:14][N:15]1[C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[C:11]=2[C:2]([CH3:1])=[CH:3][C:4]1=[O:5]

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 12333358HCID 12333358, compound

Product 1

HCID 15924245HCID 15924245, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-9 °C

Procedure

4.46 g (0.025 mol) of 4-methyl-5,6,7,8-tetrahydro- cumarin-5-one are dissolved in a mixture of 41.9 g of liquid methylamine in 100 ml of methanol pre- cooled to -9° C., With cooling, and heated to 180° C. for 3 hours in an autoclave. After cooling the methanol and methylamine are distilled off using a rotary evaporator, the residue is chromatographed on a silica gel column using ethylene chloride/ethanol (95:5) and recrystallised from cyclohexane/ethyl acetate (1:1).

Workup

  1. temperatureWith cooling
  2. temperatureheated to 180° C. for 3 hours in an autoclave
  3. distillationare distilled off
  4. customa rotary evaporator
  5. customthe residue is chromatographed on a silica gel column
  6. customrecrystallised from cyclohexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-90b9317abe044c5780ff861c50340a73
Source dataset
uspto-grants-1991_11
Patent number
US05068334

Reaction notes

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