Tin tetrachloride dihydrate → HCID 87330185, compound

HRID 1040614Notes

Reaction equation

HRID 1040614 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:12](=[CH:13][CH:14]=1)[CH:11]1[O:15][CH:7]2[CH2:8][N:9]([CH2:16][C:17]#[CH:18])[CH2:10]1)([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:16]([N:9]1[CH2:8][CH:7]2[O:15][CH:11]([C:12]3[C:6]2=[CH:5][C:4]([NH2:1])=[CH:14][CH:13]=3)[CH2:10]1)[C:17]#[CH:18]

Participants

5

Reactant 2

HCID 85782573Tin tetrachloride dihydrateHCID 87330275HCID 87330275, compound

Product 1

HCID 87330185HCID 87330185, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

4-Nitro-10-prop-2-ynyl-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (120 mg, 0.49 mmol) and tin chloride dihydrate (554 mg, 2.45 mmol) were heated at reflux in EtOAc (10 mL) for 2 h. The resulting mixture was then diluted with saturated aqueous NaHCO3 (10 mL), extracted with EtOAc (2×15 mL), dried over MgSO4, filtered and concentrated to obtain 10-Prop-2-ynyl-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-trien-4-ylamine as a brown, viscous oil (71 mg, 68%). MS (m/e) 215 (M+1)

Workup

  1. extractionextracted with EtOAc (2×15 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-24edaffb8f274f51b31166b63de1035d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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