Methanesulfonyl chloride → HCID 19968571, compound

HRID 975925Notes

Reaction equation

HRID 975925 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:15])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]#[N:14])[CH2:8][CH2:7][CH2:6]2.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1.CCOC(C)=O>[C:13]([CH:9]1[CH2:8][CH2:7][CH2:6][C:5]2[C:4]([NH:15][S:17]([CH3:16])(=[O:19])=[O:18])=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]1=2)#[N:14]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20222960HCID 20222960, compound

Product 1

HCID 19968571HCID 19968571, compoundYield 445.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-methoxy-5-amino-1, 2,3,4 -tetrahydronaphthalene-1-carbonitrile (1.7 g, 8.3 mmol) in 20 ml of anhydrous pyridine was added methanesulfonyl chloride (1.9 ml, 1.2 mmol). The resulting solution was stirred for 2 h at 25° C. The reaction mixture was concentrated in vacuo to yield an oily residue which was redissolved in EtOAc and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and concentrated in vacuo to provide an oily residue which was purified by column chromatography (EtOAc, neat) to yield 1.5 g (65%) of the desired product. 1H NMR (300 MHz, CDCl3): δ 6 1.82 (m, 1H), 1.94 (m, 1H), 2.14 (m, 2H), 2.96 (s, 3H), 3.03 (q, 2H, J=8.8 Hz), 3.84 (s, 3H), 3.96 (t, 1H, J=6.3 Hz), 6.85 (d, 1H, J=8.9 Hz), 7.39 (d, 1H, J=8.9 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto yield an oily residue which
  3. washwashed with aqueous NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto provide an oily residue which
  7. customwas purified by column chromatography (EtOAc, neat)

Sources & evidence

ORD record
ord-43972eaa1e034baf867fbb1155c766e5
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

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