Hydroxyamine hydrochloride → HCID 66963304, compound

HRID 1363305Notes

Reaction equation

HRID 1363305 reaction equation
[CH:1]([C:3]1[C:7]2[NH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:6]=2[O:5][CH:4]=1)=O.Cl.[NH2:15]O>CN(C=O)C>[C:1]([C:3]1[C:7]2[NH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:6]=2[O:5][CH:4]=1)#[N:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 59648520HCID 59648520, compound

Product 1

HCID 66963304HCID 66963304, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 3-formyl-4H-furo[3,2-b]pyrrole-5-carboxylic acid (0.20 g, 0.2 M, 1.12 mmol) in DMF (6.0 mL) was added hydroxylamine hydrochloride (0.16 g, 2.24 mmol). The reaction mixture was heated at 125° C. overnight, then cooled to rt. The mixture was partitioned between EtOAc (20 mL) and H2O (20 mL). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic phases were washed with H2O and saturated aq NaCl, filtered and concentrated in vacuo. The crude product was chromatographed over silica gel (0 to 40% MeOH in CH2Cl2 over 30 min) to give 3-cyano-4H-furo[3,2-b]pyrrole-5-carboxylic acid 51 (4 mg, 2.1%) as a brown solid. 1H NMR (400 MHz, CD3OD) δ ppm 6.65 (d, J=0.68 Hz, 1H) 7.33 (d, J=0.68 Hz, 1H). LCMS m/e 175 (M−H).

Workup

  1. temperaturecooled to rt
  2. customThe mixture was partitioned between EtOAc (20 mL) and H2O (20 mL)
  3. extractionThe aqueous phase was extracted with EtOAc (3×20 mL)
  4. washThe combined organic phases were washed with H2O and saturated aq NaCl
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed over silica gel (0 to 40% MeOH in CH2Cl2 over 30 min)

Sources & evidence

ORD record
ord-fe4d21301a6946e6bbadf282f6ec1a75
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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