Sulfuric Acid → HCID 58479580, compound

HRID 1517001Notes

Reaction equation

HRID 1517001 reaction equation
[Cl:1][C:2]1[C:7](N)=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15]C)[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.CC([N+]([O-])=O)(C)C>C(O)(=O)C>[Cl:1][C:2]1[C:7]2[O:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 116722-Methyl-2-nitropropaneHCID 86658616HCID 86658616, compound

Product 1

HCID 58479580HCID 58479580, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

2-chloro-4-(2-methoxyphenyl)pyridin-3-amine (4.3 g, 18 mmol) was dissolved in 91 mL glacial acetic acid and conc. sulfuric acid (0.503 ml, 18.11 mmol). 2-methyl-2-nitropropane (6.22 g, 54.3 mmol) was added dropwise to the reaction mixture at room temperature. Reaction mixture was stirred at 45° C. until the starting material disappears in GC. After complete reaction, most of the acetic acid was distilled out under vacuum and the crude was diluted with DCM. Organic residue was partitioned between DCM and Na2CO3 solution. Organic layer was isolated, washed with brine, dried over anhd. Na2SO4 and solvents were evaporated under vacuum. Crude product was purified by silica gel column chromatography using 10-30% ethyl acetate/hexanes as eluent. 1.5 g 1-chlorobenzofuro[2,3-c]pyridine was isolated as white solid in 41% yield.

Workup

  1. customReaction mixture
  2. customAfter complete reaction
  3. distillationmost of the acetic acid was distilled out under vacuum
  4. additionthe crude was diluted with DCM
  5. customOrganic residue was partitioned between DCM and Na2CO3 solution
  6. customOrganic layer was isolated
  7. washwashed with brine
  8. customdried over anhd
  9. customNa2SO4 and solvents were evaporated under vacuum
  10. customCrude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-456f511a68834ed3a19dbda3f79549e3
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

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