Hydrochloric Acid → HCID 66859388, compound

HRID 1803132Notes

Reaction equation

HRID 1803132 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[O:16][N:15]=[C:14]([CH3:17])[CH:13]=1.[Sn](Cl)Cl.Cl.CO>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[C:12]1[O:16][N:15]=[C:14]([CH3:17])[CH:13]=1)[NH2:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24479Stannous ChlorideHCID 66858326HCID 66858326, compound

Product 1

HCID 66859388HCID 66859388, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step H (2): 5-(2-Methoxy-4-nitrophenyl)-3-methylisoxazole (750 mg, 3.2 mmol) was added portionwise (exotherm observed) to a stirred mixture of tin(II) chloride (3.0 g), concentrated hydrochloric acid (3.0 mL), methanol (3.8 mL), and THF (15 mL). The resulting mixture was stirred at rt for 3 h. The solvent was removed in vacuo. The residue diluted with water and extracted with MTBE. The aqueous layer was basified with 10% NaOH solution to pH 13. The basic solution was extracted with chloroform. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford 3-methoxy-4-(3-methylisoxazol-5-yl)aniline (550 mg, 84% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue diluted with water
  3. extractionextracted with MTBE
  4. extractionThe basic solution was extracted with chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e547fc36bacd416e85facee6f1178f2c
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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