Formic Acid → HCID 14349078, compound

HRID 346069Notes

Reaction equation

HRID 346069 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH:7]2[C:13]3[CH:14]=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:12]=3[CH2:11][CH2:10][NH:9][CH2:8]2)=[CH:4][CH:3]=1.C=[O:25].[CH:26]([OH:28])=[O:27]>O.C(=O)([O-])[O-].[Na+].[Na+]>[C:16]([OH:18])(=[O:25])/[CH:17]=[CH:12]\[C:26]([OH:28])=[O:27].[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH:7]2[C:13]3[CH:14]=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:12]=3[CH2:11][CH2:10][N:9]([CH3:26])[CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 14349075HCID 14349075, compound

Product 1

HCID 14349078HCID 14349078, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
75 °C

Procedure

1-(4-Chlorophenoxy)-7,8-dimethoxy-2,3,4,5-tetrahydro-3-benzazepine (3 g, 6 mmole) was dissolved in 9 ml 95% formic acid and to this was added 8 ml 37% formaldehyde solution. The mixture was stirred at 75° C. for one hour, then was cooled, diluted with water and basified with sodium carbonate. The oil which separated was extracted with ether, washed with water, saturated NaCl, was dried (anhydrous MgSO4), filtered and evaporated to 2.1 g of an oil. This oil was converted to the maleate salt and recrystallized from isopropanol-ether to give 1.9 g (68%) of 1-(4-chlorophenoxy)-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-3-benzazepine maleate, d 153°-154° C.

Workup

  1. temperaturewas cooled
  2. customThe oil which separated
  3. extractionwas extracted with ether
  4. washwashed with water, saturated NaCl
  5. dry with materialwas dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. customevaporated to 2.1 g of an oil
  8. customrecrystallized from isopropanol-ether

Sources & evidence

ORD record
ord-15f26926f4394185b98762e724e1a604
Source dataset
uspto-grants-1991_10
Patent number
US05059688

Reaction notes

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