Formaldehyde → HCID 20310623, compound

HRID 1763651Notes

Reaction equation

HRID 1763651 reaction equation
N[C:2]1[CH:16]=[CH:15][C:5]2[CH:6]=[CH:7][N:8]3[CH:14]=[CH:13][CH:12]=[C:9]3[C:10](=[O:11])[C:4]=2[CH:3]=1.C=O.[C:19](#N)C.[C:22]([BH3-])#[N:23].[Na+]>C(O)(=O)C>[CH3:19][N:23]([CH3:22])[C:2]1[CH:16]=[CH:15][C:5]2[CH:6]=[CH:7][N:8]3[CH:14]=[CH:13][CH:12]=[C:9]3[C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 20310593HCID 20310593, compound

Product 1

HCID 20310623HCID 20310623, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 9-amino-11H-pyrrolo[2,1-b][3]benzazepin-11-one (2.1 g., 10 mmoles) and 4 ml. (50 mmole) of 37% aqueous formaldehyde in 15 ml. of acetonitrile 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 mins. and then glacial acetic acid is added dropwise until the solution tests neutral on wet pH paper. Stirring is maintained for an additional 2 hrs. 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-11H-pyrrolo[2,1-b][3]benzazepin-11-one as a dark brown oil.

Workup

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

Sources & evidence

ORD record
ord-51fa0aaa651e4d64a7e5dcc18a8a5240
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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