Hydrochloric Acid → 7-(benzyloxy)-9H-carbazol-2-amine

HRID 1879536Notes

Reaction equation

HRID 1879536 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([NH:22]C(=O)OC(C)(C)C)=[CH:17][C:18]=3[NH:19]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([NH2:22])=[CH:17][C:18]=3[NH:19]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66933893tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate

Product 1

HCID 592829487-(benzyloxy)-9H-carbazol-2-amineYield 102%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate (200 mg, 0.51 mmol) was added 10 mL of a 4 M HCl in dioxane solution. The mixture was stirred at rt for 4 h and concentrated under reduced pressure. The residue was washed with ether (15 mL) and suspended in EtOAc (50 mL). To this suspension was added 10 mL of a NaHCO3 (sat.) and the mixture was stirred for 5 min. The organic layer was dried over MgSO4 and concentrated to afford 7-(benzyloxy)-9H-carbazol-2-amine as a brown solid (150 mg, 100%). 1H NMR (400 MHz, DMSO-d6) δ 11.33 (s, 1H), 7.99 (d, J=8.4 Hz, 1H), 7.92 (d, J=8.8 Hz, 1H), 7.42 (d, J=6.8 Hz, 2H), 7.34-7.21 (m, 3H), 7.27-7.23 (m, 1H), 7.00-6.97 (m, 2H), 6.81 (dd, J=8.8, 2.4 Hz, 1 H), 5.12 (s, 2H); MS (ESI) m/z 289 (M+H+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe residue was washed with ether (15 mL)
  3. additionTo this suspension was added 10 mL of a NaHCO3 (sat.)
  4. stirringthe mixture was stirred for 5 min
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-45c06af874964df794eeb8f4abc0a097
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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