Ammonia → HCID 68934147, compound

HRID 749219Notes

Reaction equation

HRID 749219 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[CH2:11][C:12]([NH:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=1[CH:17]=[CH:18]O[C:20]3=[O:25])=[O:13])[CH2:8]2.[NH3:26]>C(O)C>[CH:3]12[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:1]([CH2:10]3)[CH:2]1[CH2:11][C:12]([NH:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=1[CH:17]=[CH:18][NH:26][C:20]3=[O:25])=[O:13])[CH2:9]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68933965HCID 68933965, compound

Product 1

HCID 68934147HCID 68934147, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
115 °C

Procedure

90 mg (0.27 mmol) of 2-adamantyl-N-(1-oxo-1H-isochromen-5-yl)acetamide (1) was treated with 10 mL (20 mmol) of a 2 M ammonia solution in ethanol at room temperature in a resealable tube. The reaction vessel was sealed and heated at 115° C. for 48 h. After the reaction mixture was cooled down to room temperature, the solvent was evaporated and residue obtained was purified by prep. HPLC to yield 2-adamantyl-N-(1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide (2a) (41 mg, 0.122 mmol, 45%) as an off-white powder. HPLC ret. time 2.07 min, 10-100% CH3CN, 3.5 min gradient; ESI-MS m/z 337.2 (M+H)+.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter the reaction mixture was cooled down to room temperature
  3. customthe solvent was evaporated
  4. customresidue obtained
  5. customwas purified by prep

Sources & evidence

ORD record
ord-316976dcfed447e4ba603bb0a609afc7
Source dataset
uspto-grants-2008_07
Patent number
US07402596B2

Reaction notes

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