Formaldehyde → HCID 20310637, compound

HRID 616613Notes

Reaction equation

HRID 616613 reaction equation
N[C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH2:7][N:8]3[CH:14]=[CH:13][CH:12]=[C:9]3[C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:17]=O.[C:19]([BH3-])#[N:20].[Na+]>C(O)(=O)C>[CH3:17][N:20]([CH3:19])[C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH2:7][N:8]3[CH:14]=[CH:13][CH:12]=[C:9]3[C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 13152894HCID 13152894, compound

Product 1

HCID 20310637HCID 20310637, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 9-amino-6,11-dihydro-5H-pyrrolo-[2,1-b][3]benzazepin-11-one (2.1 g., 10 mmoles) and 4 ml. (50 mmoles) of 37% aqueous formaldehyde in 15 ml. of acetonitrite is added 1 g. (16 mmoles) of sodium cyano borohydride. A vigorous and exothermic reaction takes place and a dark residue separates. The mixture is stirred for 15 minutes and then glacial acetic acid is added dropwise until the solution tests neutral on wet pH paper. Stirring is maintained for an additional 2 hours. The volatiles are removed under vacuum, and the residue is dissolved in chloroform. The solution is washed with base and with water, dried over sodium sulfate, and concentrated to leave a residue that is purified by chromatography on silica gel. Elution with chloroform yields 9-dimethylamino-6,11-dihydro-5H-pyrrolo [2,1-b][3]benzazepin-11one as a dark brown oil.

Workup

  1. additionof acetonitrite is added 1 g
  2. customA vigorous and exothermic reaction
  3. stirringStirring
  4. temperatureis maintained for an additional 2 hours
  5. customThe volatiles are removed under vacuum
  6. dissolutionthe residue is dissolved in chloroform
  7. washThe solution is washed with base and with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto leave a residue that
  11. customis purified by chromatography on silica gel
  12. washElution with chloroform

Sources & evidence

ORD record
ord-881b9a767a6944e8ac0ee6a9c4112e40
Source dataset
uspto-grants-1978_02
Patent number
US04075225

Reaction notes

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