Hydroxyamine hydrochloride → HCID 178471588, compound

HRID 423337Notes

Reaction equation

HRID 423337 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:2].[NH2:20][OH:21].Cl.C([O-])(O)=O.[Na+]>CCO>[OH:21][NH:20][C:1](=[NH:2])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium Bicarbonate2×HCID 59318426Ethyl 4-(4-cyano-1H-indol-1-yl)butanoate

Product 1

HCID 178471588HCID 178471588, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

Ethyl 4-(4-cyano-1H-indol-1-yl)butanoate (D56) (8.25 g, 32.2 mmol) was dissolved in EtOH and treated with NH2OH.HCl (4.47 g, 64.4 mmol) and NaHCO3 (8.11 g, 97 mmol) and heated to 55° C. for 1 day and two nights. Further NH2OH.HCl (500 mg) and NaHCO3 (500 mg) were added and the reaction was heated for another 3 hours and then separated the inorganics by filtration, washing well with EtOH. The solvent was evaporated and the residue dried under high vacuum. Trituration with ether and dcm afforded two batches of the title compound N2668-20-A8 (5.14 g) and N2668-20-A9 (976 mg). δH (400 MHz, d6-DMSO) 1.15 (3H, t), 1.98 (2H, apparent quin), 2.25 (2H, t), 4.03 (2H, q), 4.21 (2H, t), 5.73 (2H, br s), 6.82 (1H, dd), 7.15 (1H, apparent t), 7.27 (1H, dd), 7.35 (1H, d), 7.51 (1H, d), 9.58 (1H, br s). MS (ES): C15H19N3O3 requires 289; found 290 (MH+).

Workup

  1. temperaturethe reaction was heated for another 3 hours
  2. customseparated the inorganics
  3. filtrationby filtration
  4. washwashing well with EtOH
  5. customThe solvent was evaporated
  6. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-04d86e8191154bb386a17faf7dd59138
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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