hydroxylamine-O-sulfonic acid → HCID 178453019, compound

HRID 76819Notes

Reaction equation

HRID 76819 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[C:6]([O:10][C:11]([NH:13][CH2:14][C:15]1[C+:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]1[CH2:24][CH:25]=[C:26]([CH:28]=[CH:29][N:30](C)C)[CH:27]=[C:19]1[C:18]2([CH3:34])[CH3:33])=[O:12])([CH3:9])([CH3:8])[CH3:7].NOS(O)(=O)=O.C(=O)(O)[O-].[Na+]>CO.O>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[C:6]([O:10][C:11]([NH:13][CH2:14][C:15]1[C+:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]1[CH2:24][CH:25]=[C:26]([CH2:28][C:29]#[N:30])[CH:27]=[C:19]1[C:18]2([CH3:34])[CH3:33])=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 76284hydroxylamine-O-sulfonic acidHCID 516892Sodium BicarbonateHCID 178483368HCID 178483368, compound

Product 1

HCID 178453019HCID 178453019, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

2-(tert-Butoxycarbonylamino-methyl)-8-(2-dimethylamino-vinyl)-10,10-dimethyl-10H-pyrido[1,2-a]indolylium perchlorate (14 g, 0.028 mol; Sigma-Aldrich) was placed into 500-mL conical flask equipped with magnetic stir bar followed by 400 mL of 1:1 MeOH—H2O mixture. Stirring was started and hydroxylamine-O-sulfonic acid (14 g, 0.12 mol; Aldrich) was added to the flask in one portion. In about 2 hours all solid was dissolved and stirring was continued for additional 48 hours at room temperature. Sodium bicarbonate (2.00 g) was added to the reaction mixture to adjust pH equal to 7.0. The reaction mixture was transferred into 1-L round bottom one-necked flask and 80% of the reaction solvent was evaporated under vacuum. The product deposited on flask wall as a slightly yellow tar. The aqueous solution (ca 80-100 mL) that contained excess of hydroxylalamino sulfonic acid was discarded and the deposited tar was washed with water (2*60 mL) and dissolved in 250 mL water-methanol (1:1) mixture. Most of the solvent was again removed in vacuum, aqueous solution (approximately 50 mL) discarded, the separated organic residue was washed with water (2*60 mL), ether and dried. The crude product was used in the next step without additional purification. The yield of crude material was 13.1 g (100% of theory).

Workup

  1. customequipped with magnetic stir bar
  2. dissolutionIn about 2 hours all solid was dissolved
  3. stirringstirring
  4. customwas evaporated under vacuum
  5. customThe product deposited on flask
  6. washthe deposited tar was washed with water (2*60 mL)
  7. dissolutiondissolved in 250 mL water-methanol (1:1) mixture
  8. customMost of the solvent was again removed in vacuum, aqueous solution (approximately 50 mL)
  9. washthe separated organic residue was washed with water (2*60 mL), ether
  10. customdried
  11. customThe crude product was used in the next step without additional purification

Sources & evidence

ORD record
ord-21de2879651e47ca8f51bce96648a4f7
Source dataset
uspto-grants-2014_09
Patent number
US08835632B2

Reaction notes

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