Hydrochloric Acid → HCID 58494705, compound

HRID 516218Notes

Reaction equation

HRID 516218 reaction equation
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:18]([O-])=O.Cl.[OH-].[Na+]>CCO>[NH2:18][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][N:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10][CH2:11][C:12]=2[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58494611HCID 58494611, compound

Product 1

HCID 58494705HCID 58494705, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 6.431 g of ethyl 6-chloro-7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate was added 120 ml of EtOH, followed by stirring at 60° C. for dissolution, and 12.15 g of reduced iron and 60 ml of 1 M hydrochloric acid were added thereto, followed by heating and refluxing for 1 hour. The reaction mixture was alkalified by the addition of a 1 M aqueous sodium hydroxide solution and then filtered through celite, and then the organic solvent was evaporated under reduced pressure. The residue was extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure to obtain 5.743 g of ethyl 7-amino-6-chloro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate as a reddish orange viscous substance.

Workup

  1. additionwere added
  2. temperatureby heating
  3. temperaturerefluxing for 1 hour
  4. filtrationfiltered through celite
  5. customthe organic solvent was evaporated under reduced pressure
  6. extractionThe residue was extracted with chloroform
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-74d441c7e0d4489f999ef2e6b5dd3ff3
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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