Formic Acid → HCID 14685751, compound

HRID 1088804Notes

Reaction equation

HRID 1088804 reaction equation
[O:1]=[C:2]1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[CH:12]([NH:15][CH2:16][CH:17]=[CH2:18])[CH2:13][CH2:14][N:3]1[C:4]=23.[CH:19](O)=O>C=O>[O:1]=[C:2]1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[CH:12]([N:15]([CH3:19])[CH2:16][CH:17]=[CH2:18])[CH2:13][CH2:14][N:3]1[C:4]=23

Participants

4

Reactant 2

HCID 284Formic AcidHCID 14685750HCID 14685750, compound

Product 1

HCID 14685751HCID 14685751, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Conditions

Temperature
90 °C

Procedure

6,7-Dihydro-3-oxo-7-allylamino-1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine (5.86 g) was dissolved in a solution of formic acid (7 ml) and 35% formalin (7 ml), and the solution was stirred for 2 hours at 90° C. Formic acid and formalin were distilled off under reduced pressure, and to this mixture were added ice water and dichloromethane, and the mixture was adjusted to alkalinic with sodium carbonate. The mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and distilled off to give 6,7-dihydro-3-oxo-7-(N-methyl-N-allylamino)- 1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine (5.90 g).

Workup

  1. distillationFormic acid and formalin were distilled off under reduced pressure
  2. additionto this mixture were added ice water and dichloromethane
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled off

Sources & evidence

ORD record
ord-7e7b224a2ee84c50853155c269fa3520
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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