Hydroxyamine hydrochloride → HCID 10154708, compound

HRID 1362553Notes

Reaction equation

HRID 1362553 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].C[O:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:30])/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>CO>[OH:6][NH:5][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:30])/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28])=[O:8]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 57495376HCID 57495376, compound

Product 1

HCID 10154708HCID 10154708, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methylate (6.0 mmol) in methanol (5 ml) was added to a solution of hydroxylamine hydrochloride (0.28 g, 4.0 mmol) (Acros) in methanol (8 ml). The mixture was stirred for 10 min. and the precipitate was filtered off. (2E,4E)-6-[5-(2-Nitrophenyl)penta-2,4-dienoylamino]hexanoic acid methyl ester (13a) (0.35 g, 1 mmol) was added to the filtrate and the obtained mixture was heated to the complete dissolving. The resultant mixture was stirred for 4 hours at ambient temperature and the solvent was removed under reduced pressure. The product was dissolved in water (10 ml) and the solution was acidified with 3% HCl. The precipitate was filtered and crystallized from acetonitrile to give the title compound (0.23 g, 66%) as a yellow solid. M.p. 131-133° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.06-1.73 (6H, m, CH2); 1.87-2.09 (2H, m, CH2); 3.15 (2H, q, J=5.6 Hz, CH2N); 6.26 (1H, d, J=14.8 Hz, CH); 7.00-8.06 (8H, m, CH—CH═CH, C6H4, NH); 8.06 (1H, t, J=5.9 Hz, NH); 10.33 (1H, s, OH). HPLC analysis on Symmetry C18 column: impurities <1.0% (column size 3.9×150 mm; mobile phase acetonitrile −0.1 M phosphate buffer (pH 2.5), 35:65; detector UV 220 nm; sample concentration 0.15 mg/ml). Anal. Calcd for C17H21N3O5, %: 58.78, H, 6.09, N, 12.10. Found, %: C, 58.26, H, 6.08, N, 11.87.

Workup

  1. filtrationthe precipitate was filtered off
  2. temperaturethe obtained mixture was heated to the complete dissolving
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe product was dissolved in water (10 ml)
  5. filtrationThe precipitate was filtered
  6. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-0d2d3d1ac2474c51925b02af0271d1f0
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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