Ammonia → HCID 18785858, compound

HRID 1107730Notes

Reaction equation

HRID 1107730 reaction equation
C(S[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([CH3:14])[N:5]=1)C.[I-:15].[NH4+:16].N.C(OCC)C>C(O)C>[IH:15].[NH2:16][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([CH3:14])[N:5]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 25487Ammonium iodideHCID 11138233HCID 11138233, compound

Product 1

HCID 18785858HCID 18785858, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-ethylthio-3,4-dihydro-3-methylisoquinoline (M. Gittos et al, J. Chem. Soc., Perkin I, 1976, 33) (0.68 g, 3.3 mmol), ammonium iodide (0.48 g, 3.3 mmol) and ammonia (2M in methanol, 4 ml) in ethanol (4 ml) was heated at reflux for 4 h. The mixture was allowed to cool and diethyl ether (100 ml) was added. Some dark oil which separated on standing was decanted and the remaining clear solution stood at -20 ° for 24 h. The resulting crystals were collected, washed with diethyl ether and dried to afford the product as pale yellow prisms (370 mg), m.p. 114-116° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperatureto cool
  4. customSome dark oil which separated on standing
  5. customwas decanted
  6. customThe resulting crystals were collected
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-0e4329f0f3ad44f0b8ca01bf5a645a08
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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