Water → HCID 14349109, compound

HRID 2107716Notes

Reaction equation

HRID 2107716 reaction equation
[C:1](O)(=O)/C=C\[C:4]([OH:6])=[O:5].[CH3:9][O:10][C:11]1[C:31]([O:32][CH3:33])=[CH:30][C:14]2[CH:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[CH2:16][NH:17][CH2:18][CH2:19][C:13]=2[CH:12]=1.O.[C:35](=[O:38])([O-:37])[O-].[Na+].[Na+]>C(O)=O.C=O>[C:4]([OH:6])(=[O:5])[C:35]([OH:37])=[O:38].[CH3:9][O:10][C:11]1[C:31]([O:32][CH3:33])=[CH:30][C:14]2[CH:15]([O:20][C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)[CH2:16][N:17]([CH3:1])[CH2:18][CH2:19][C:13]=2[CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 14820767HCID 14820767, compound

Product 1

HCID 14349109HCID 14349109, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Procedure

A solution of 7,8-dimethoxy-1-(4-nitrophenoxy)-2,3,4,5-tetrahydro-3-benzazepine of Example 49, (6 g, 17.4 mmole) in 25 ml 95% formic acid and 25 ml 37% aqueous formaldehyde solution was stirred at 75° C. for 1.5 hours. After cooling, the reaction mixture was stirred with water, basified with sodium carbonate and was extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride and was dried (anhydrous MgSO4), filtered and evaporated to 6.2 g of an oil. This oil was purified by high pressure liquid chromatography (silica gel, ethyl acetate) to give 4.6 g (74%) of an oil. This oil was converted to the oxalate salt as in Example 1 and was twice recrystallized from isopropanol-methanol to give 3.4 g (44%) of 7,8-dimethoxy-3-methyl-1-(4-nitrophenoxy)-2,2,4,5-tetrahydro-3-benzazepine oxalate, d 158°-159° C.

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water and saturated sodium chloride
  5. dry with materialwas dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. customevaporated to 6.2 g of an oil
  8. customThis oil was purified by high pressure liquid chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-ba83e05d03dd47ea9e4d500504e711c3
Source dataset
uspto-grants-1990_06
Patent number
US04935418

Reaction notes

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