Methanol → HCID 178490756, compound

HRID 351851Notes

Reaction equation

HRID 351851 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=4[O:24][CH3:25])[C:13](=[O:14])[C:4]=2[CH:3]=1)=[C:9]([C:26]#[N:27])[N:8]=[CH:7]3.Cl.[NH2:31][OH:32].C[O-].[Na+].CO>CN(C=O)C.O>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=4[O:24][CH3:25])[C:13](=[O:14])[C:4]=2[CH:3]=1)=[C:9]([C:26]([NH:31][OH:32])=[NH:27])[N:8]=[CH:7]3

Participants

7

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 22713467HCID 22713467, compound

Product 1

HCID 178490756HCID 178490756, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8-Chloro-5-(2,4-dimethoxy-benzyl)-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carbonitrile (2 g, 4.9 mmol) and hydroxylamine HCl (1 g, 14.6 mmol) were suspended in DMF (10 mL) and treated slowly with a 5.4 M solution of sodium methylate in methanol (2.7 mL, 14.6 mmol). The yellow suspension was stirred overnight. The suspension was cooled in ice and diluted with water (20 mL) and stirred for 1 h in ice. The crystals were filtered off and washed with cold water (5 mL). One obtained white crystals (1.9 g, 89%). m/z 442 (MH+).

Workup

  1. temperatureThe suspension was cooled in ice
  2. stirringstirred for 1 h in ice
  3. filtrationThe crystals were filtered off
  4. washwashed with cold water (5 mL)

Sources & evidence

ORD record
ord-1b5133cdb1cc4ad8a0ae78384a543747
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

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