Hydrochloric Acid → HCID 10750709, compound

HRID 430929Notes

Reaction equation

HRID 430929 reaction equation
[Sn].[CH3:2][O:3][C:4]1[C:5]([N+:16]([O-])=O)=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH:8]=[C:7]2[CH:14]=[O:15].Cl>CCO>[NH2:16][C:5]1[C:4]([O:3][CH3:2])=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([CH:14]=[O:15])=[CH:8][N:9]2[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 108472805-Methoxy-1-Methyl-4-Nitroindole-3-Carboxaldehyde

Product 1

HCID 10750709HCID 10750709, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin powder (2.65 g, 22.3 mmol) was added to a suspension of nitroindole 44 (600 mg, 2.56 mmol) in EtOH (90 mL). Hydrochloric acid (3 M, 36 mL) was added and the mixture was stirred at room temperature for 2 h. The reaction mixture was decanted from the excess tin and added in portions to saturated sodium bicarbonate (200 mL). The mixture was extracted with EtOAc (4×) and the combined extracts were washed with sodium bicarbonate (1 M, 3×) and saturated NaCl (2×), dried (MgSO4), filtered and evaporated. Compound 45 was isolated as a dark yellow oil (513 mg, 98%) and used in the following reaction without further purification; Rf=0.67 (EtOAc); 1H NMR (CDCl3): δ 9.61 (s, 1H), 7.55 (s, 1H), 6.94 (d, 1H, J=8.6 Hz), 6.53 (d, 1H, J=8.6 Hz), 5.79 (bs, 2H), 3.88 (s, 3H), 3.76 (s, 3H).

Workup

  1. customThe reaction mixture was decanted from the excess tin
  2. additionadded in portions to saturated sodium bicarbonate (200 mL)
  3. extractionThe mixture was extracted with EtOAc (4×)
  4. washthe combined extracts were washed with sodium bicarbonate (1 M, 3×) and saturated NaCl (2×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-acf599ce18cb483ba3b61d2af7a224cb
Source dataset
uspto-grants-2003_12
Patent number
US06656926B2

Reaction notes

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