Formaldehyde → HCID 22620531, compound

HRID 840983Notes

Reaction equation

HRID 840983 reaction equation
C=O.[B-][C:4]#N.[Na+].[NH:7]1[CH2:13][CH2:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]1=2.[OH-].[Na+]>C(#N)C.C(O)(=O)C>[CH3:4][N:7]1[CH2:13][CH2:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]1=2

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 15549909HCID 15549909, compoundHCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 22620531HCID 22620531, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A 37% aqueous formaldehyde solution (1.50 g, 18.4 mmol), sodium cyanotrihydroborate (0.12 g, 18.4 mmol) and acetic acid (0.1 ml) were added to a solution in acetonitrile (8 ml) of the ethyl 2,3-dihydro-1H-benz[b]azepine-4-carboxylate (0.40 g, 1.84 mmol) synthesized in Reference Example 5. After stirring at room temperature for 2 hours, the reaction mixture was poured into a 1N aqueous sodium hydroxide solution and extracted twice with diethyl ether. The extract solution was washed twice with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=4/96) to obtain 0.40 g of ethyl 1-methyl-2,3-dihydro-1H-benz[b]azepine-4-carboxylate.

Workup

  1. customsynthesized in Reference Example 5
  2. extractionextracted twice with diethyl ether
  3. washThe extract solution was washed twice with a 5% aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=4/96)

Sources & evidence

ORD record
ord-ab27365502b246e9b487e00d81deed12
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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