Sulfuric Acid → HCID 22285030, compound

HRID 1061523Notes

Reaction equation

HRID 1061523 reaction equation
[Cl:1][C:2]1[C:3]([NH:16][CH2:17][C:18]#[CH:19])=[N:4][C:5]2[CH:6]=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][C:10]=2[N:11]=1.OS(O)(=O)=O.[OH-].[Na+]>>[Cl:1][C:2]1[C:3]2[N:4]([C:18]([CH3:19])=[CH:17][N:16]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=1[CH:6]=2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22285037HCID 22285037, compound

Product 1

HCID 22285030HCID 22285030, compoundYield 30%

Conditions

Temperature
80 °C

Procedure

2-Chloro-3-(propargylamino)benzo[g]quinoxaline (0.420 g, 1.57 mmol) was treated with 4 mL of concentrated H2SO4 and the mixture was stirred at 80° C. for 1 hour, cooled to RT and poured into ice water. The mixture was cautiously neutralized with aqueous NaOH, and the resulting precipitate was filtered, washed with water, and dried in vacuo to give the title compound as a beige solid (0.124 g, 30%); mp 221-223° C.; IR (KBr, cm−1) 1538, 1479, 1456, 1398, 1101, 919; 1H NMR (DMSO) δ 8.79 (s, 1H), 8.53 (s, 1H), 8.23 (d, J=8.1, 1H), 8.13 (d, J=8.5, 1H), 7.69-7.59 (m, 3H), 3.04 (s, 3H); LC/MS 100% (220 nm), m/z (M+H+) 268.

Workup

  1. temperaturecooled to RT
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8b4ef0d707a04690aee984c6ce91c764
Source dataset
uspto-grants-2005_11
Patent number
US06960585B2

Reaction notes

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