Phosphoric Acid → HCID 57474458, compound

HRID 2043511Notes

Reaction equation

HRID 2043511 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[CH3:13][N:14]1[CH:18]2[CH2:19][C:20]([CH2:22][CH:15]1[CH2:16][CH2:17]2)=O.OP(O)(O)=O>C(O)(=O)C>[CH3:13][N:14]1[CH:15]2[CH2:16][CH2:17][CH:18]1[CH2:19][C:20]([C:7]1[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][CH:8]=1)=[CH:22]2

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 225235-NitroindoleHCID 79038Npc164516

Product 1

HCID 57474458HCID 57474458, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 5-nitroindole (38) (0.5 g, 3.083 mmol) in glacial acetic acid (10 mL) was treated with tropinone (0.85 g, 6.617 mmol), followed by 2 M H3PO4 in glacial acetic acid (5 mL) at 100° C. and the resulting solution was stirred at same temperature for 24 h. The reaction was brought to room temperature, poured in to ice-cold 10% NH4OH solution (50 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (15 mL) and dried (Na2SO4). The solvent was evaporated and crude material was purified by column chromatography on silica gel (2 M NH3 in methanol: CH2Cl2, 1:9) to obtain compound 89 (0.27 g, 31%) as a solid. mp 234-236° C.; 1H NMR (DMSO-d6) δ 1.51-1.60 (m, 1H), 1.79-1.86 (m, 1H), 1.95-2.14 (m, 4H), 2.32 (s, 3H), 2.76-2.83 (m, 1H), 3.43 (t, 1H, J=5.4 Hz), 6.31 (d, 1H, J=5.1 Hz), 7.54 (d, 1H, J=8.7 Hz), 7.61 (s, 1H), 8.01 (dd, 1H, J=2.1, 9.0 Hz), 8.68 (d, 1H, J=2.4 Hz), 11.86 (s, 1H); ESI-MS m/z (%): 284 (MH+, 100).

Workup

  1. customwas brought to room temperature
  2. extractionwas extracted into CH2Cl2 (2×25 mL)
  3. washThe combined CH2Cl2 layer was washed with brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customcrude material was purified by column chromatography on silica gel (2 M NH3 in methanol: CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-256ec17a31c3481595d7d5e89481eedd
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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