Hydrochloric Acid → HCID 13012490, compound

HRID 1242903Notes

Reaction equation

HRID 1242903 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O.Cl.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>CO.[Fe].C(OCC)(=O)C.O1CCCC1>[C:23]([NH:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)(=[O:25])[CH3:24]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 384457-Nitro-1-tetralone

Product 1

HCID 13012490HCID 13012490, compoundYield 84.1%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Nitro-1-tetralone (8.32 g, 0.044 mol) and concentrated hydrochloric acid (24 ml, 0.29 mol) were dissolved in methanol (100 ml), and an iron powder (7.30 g, 0.13 mol) was gradually added over 1 hour. After stirring for 1 hour, the reaction mixture was concentrated. 4N Sodium hydroxide solution and ethyl acetate were added to the residue, and extraction was conducted. The organic layer was dried, and concentrated. Tetrahydrofuran (100 ml) and triethylamine (5.05 g, 0.05 mol) was added to the residue. Further, acetyl chloride (3.92 g, 0.05 mol) was added under ice-cooling. After stirring for 30 minutes, ethyl acetate and 1N hydrochloric acid were added, and extraction was conducted. The organic layer was concentrated, and the residue was purified with silica gel column chromatography (development solvent: ethyl acetate), to give 7-acetylamino-1-tetralone (7.52 g) as a white powder.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. addition4N Sodium hydroxide solution and ethyl acetate were added to the residue, and extraction
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. temperaturecooling
  6. stirringAfter stirring for 30 minutes
  7. extractionextraction
  8. concentrationThe organic layer was concentrated
  9. customthe residue was purified with silica gel column chromatography (development solvent: ethyl acetate)

Sources & evidence

ORD record
ord-59620afc6587435a9a10329dfdf53e64
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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