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Formic Acid → HCID 14349078, compound

HRID 2107711
Notes
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Reaction equation

HRID 2107711 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 Carbonate
Solvent

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 isoproponal-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 isoproponal-ether

Sources & evidence

ORD record
ord-7a52dd7681fc4a79b2253974b9eefeed
Source dataset
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04935418

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes