Methylamine → HCID 57722504, compound

HRID 1986618Notes

Reaction equation

HRID 1986618 reaction equation
[O:1]=[C:2]1[CH2:11][C:10]2[CH:9]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[CH3:16][NH2:17]>C(Cl)Cl>[CH3:16][NH:17][S:12]([C:8]1[CH:7]=[CH:6][C:5]2[CH2:4][CH2:3][C:2](=[O:1])[CH2:11][C:10]=2[CH:9]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 55279352HCID 55279352, compound

Product 1

HCID 57722504HCID 57722504, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-oxo-5,6,7,8-tetrahydro-naphthalene-2-sulfonyl chloride (see Preparative Example 3, 1.14 g, 4.7 mmol) in CH2Cl2 (10 mL) at 15° C. (using a water bath) was added MeNH2 (2M in THF, 7 mL, 14 mmol, 3 eq) dropwise. After stirring at room temperature for 30 minutes, the mixture was diluted with CH2Cl2 (30 mL), washed with H2O (20 mL), dried (Na2SO4), and concentrated. The residue was chromatographed on silica by eluting with 20% EtOAc/hexanes to give 0.45 g (40%) of 7-oxo-5,6,7,8-tetrahydro-naphthalene-2-sulfonic acid methylamide as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.70 (d, 1H, J=8.1 Hz), 7.63 (s, 1H), 7.40 (d, 1H, J=8.1 Hz), 4.66 (q, 1H, J=5.4 Hz), 3.64 (s, 2H), 3.14 (t, 2H, J=6.6 Hz), 3.65 (d, 3H, J=5.4 Hz), 2.57 (t, 2H, J=6.6 Hz).

Workup

  1. washwashed with H2O (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica
  5. washby eluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-eef8c5daa2c645bea08c50d82ff82792
Source dataset
uspto-grants-2009_06
Patent number
US07550467B2

Reaction notes

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