Hydrochloric Acid → 5-Amino-1,3-dihydropyrrol[4,3,2-de]isoquinoline hydrochloride

HRID 1284030Notes

Reaction equation

HRID 1284030 reaction equation
C(O[C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[NH:14][CH:15]=[C:7]([C:8]=23)[CH2:6][N:5]=1)C.[OH-].[NH4+:17].[ClH:18].CCOCC>C(O)C>[NH2:17][C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[NH:14][CH:15]=[C:7]([C:8]=23)[CH2:6][N:5]=1.[ClH:18].[NH2:17][C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[NH:14][CH:15]=[C:7]([C:8]=23)[CH2:6][N:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14923Ammonium HydroxideHCID 215155225-Ethoxy-1,3-dihydropyrrolo[4,3,2-de]isoquinoline

Product 2

HCID 215155205-Amino-1,3-dihydropyrrol[4,3,2-de]isoquinoline hydrochlorideHCID 215155215-Amino-1,3-dihydropyrrolo[4,3,2-de]isoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 5-ethoxy-1,3-dihydropyrrolo[4,3,2-de]isoquinoline (200 mg, 1 mmole), described in Example 5, in ethanol (2 ml), aqueous ammonium hydroxide (25%, 0.5 ml, 1.4 mmole) is added followed by 2.3 N HCl in ethanol (0.5 ml). The mixture is heated at reflux for 0.5 hour, then ether is added and the light green crystalline precipitate collected to give the hydrochloride salt of the title compound, 5-amino-1,3-dihydropyrrol[4,3,2-de]isoquinoline hydrochloride, mp 227° - 228°C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 0.5 hour
  3. customthe light green crystalline precipitate collected

Sources & evidence

ORD record
ord-62f82ea11cf54520bb531ed43a5f9e8e
Source dataset
uspto-grants-1976_08
Patent number
US03978066

Reaction notes

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