Sulfuric acid magnesium salt (1:1) → HCID 18617552, compound

HRID 1264202Notes

Reaction equation

HRID 1264202 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]=O.Cl.[NH2:16]O.S([O-])([O-])(=O)=O.[Mg+2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C>[C:13]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([CH2:3][CH2:2][Cl:1])[CH:5]=2)[NH:9][CH:8]=1)#[N:16]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 443297Hydroxyamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 18617606HCID 18617606, compound

Product 1

HCID 18617552HCID 18617552, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3.29 g (15.8 mmol) 5-(2-chloroethyl)indole-3-carboxaldehyde (reference example 5), 1.15 g (16.6 mmol) hydroxylamine hydrochloride, 6.27 g (52.1 mmol) magnesium sulfate, and 0.601 g (3.16 mmol) p-toluenesulfonic acid monohydrate in 10 mL DMF is heated to 150° C. for 30 minutes. The reaction mixture is azeotroped with toluene, and the resulting residue chromatographed (2:1, then 1:1 hexane:ethyl acetate) to provide 3.08 g of product as a white solid in 95% yield. 1H NMR (CDCl3): δ 3.20 (2H, t, J=7 Hz), 3.77 (2H, t, J=7 Hz), 7.21 (1H, dd, J=8, 1 Hz), 7.43 (1H, d, J=8 Hz), 7.63 (1H, s), 7.73 (1H, d, J=3 Hz), 8.66 (1H, br). MS (EI) m/z 204, 206 (M[35Cl, 37Cl])+, 155 (M−CH2Cl)+.

Workup

  1. customThe reaction mixture is azeotroped with toluene
  2. customthe resulting residue chromatographed (2:1

Sources & evidence

ORD record
ord-e6e8a2766f824086ad9ac4e51009e6b6
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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