Hydroxyamine hydrochloride → HCID 11461110, compound

HRID 545462Notes

Reaction equation

HRID 545462 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:8]=2[CH:7]=1)=O)C.[NH2:24][OH:25].Cl.C[O-].[Na+]>CO>[OH:25][NH:24][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:8]=2[CH:7]=1)=[O:3]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 46416745HCID 46416745, compound

Product 1

HCID 11461110HCID 11461110, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-benzoylamino -benzo[b]thiophene-2-carboxylic acid ethyl ester (102.9 mg, 0.32 mmol) were added NH2OH.HCl (76.2 mg, 0.97 mmol) and 5 mL of anhydrous MeOH. A solution of NaOMe (4.37 M in MeOH, 0.50 mL, 2.18 mmol) was added. The resulting mixture was allowed to stir at rt for 2 days. The reaction mixture was concentrated and the residue was dissolved in a minimal amount of water. After extracted with 5 mL of hexanes/EtOAc (4:1), the aqueous layer was acidified with 2N aqueous HCl to pH≈7. The precipitate was filtered, collected and dried to give 5-benzoylamino-benzo[b]thiophene-2-carboxylic acid hydroxyamide as a pale solid. 1H NMR (DMSO-d6, 200 MHz) δ 10.41 (s, 1H), 8.44 (s, 1H), 8.10-7.82 (m, 4H), 7.76 (dd, J=8.7, 2.1 Hz, 1H), 7.68-7.35 (m, 4H). MS (EI): cal'd 313.1 (MH+), exp 313.2 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in a minimal amount of water
  3. extractionAfter extracted with 5 mL of hexanes/EtOAc (4:1)
  4. filtrationThe precipitate was filtered
  5. customcollected
  6. customdried

Sources & evidence

ORD record
ord-297a50cf298144e6bfc077601e98f037
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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