2-(2,3-Dioxo-2,3-dihydro-1H-indol-1-yl)acetamide → HCID 840219, compound

HRID 1466299Notes

Reaction equation

HRID 1466299 reaction equation
[O:1]=[C:2]1[C:10](=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][C:13]([NH2:15])=[O:14]>CS(C)=O>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][C:13]([NH2:15])=[O:14]

Participants

3

Reactant 1

HCID 19061622-(2,3-Dioxo-2,3-dihydro-1H-indol-1-yl)acetamide

Product 1

HCID 840219HCID 840219, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The above 2-(2,3-dioxoindolin-1-yl)acetamide (4.32 g) was redissolved in DMSO (20 mL) and N2H4-xH2O (2.5 mL) was added dropwise over 10 min. After addition, the resulting mixture was stirred for 5 min at rt, then 2 h at 140° C. before cooling to rt. The reaction was quenched with ice (20 mL) and 6 M HCl (8 mL), then stirred for 30 min at rt. Suction filtration gave crude title compound (2.92 g) as a light yellow solid. The product was suspended in EtOAc (120 mL) and H2O (60 mL) was added, followed by 2 M HCl (30 mL). The mixture was separated and suction filtration of aqueous layer affored the title compound as a light beige solid (1.78 g, 27% over 2 steps) after drying. 1H NMR (400 MHz, DMSO-d6) δ 7.59 (s, 1H, NH), 7.28-7.08 (m, 4H), 6.99 (t, J=7.4 Hz, 1H), 6.81 (d, J=8.0 Hz, 1H), 4.22 (s, 2H), 3.56 (s, 2H); MS ESI 191.0 [M+H]+, calcd for [C10H10N2O2+H]+ 191.1; MS ESI 174.0 [M−NH2]+, calcd for [C10H10N2O2—NH2]+ 174.1; MS ESI 146.0 [M−CONH2]+, calcd for [C10H10N2O2—CONH2]+ 146.1.

Workup

  1. additionAfter addition
  2. temperature2 h at 140° C. before cooling to rt
  3. customThe reaction was quenched with ice (20 mL) and 6 M HCl (8 mL)
  4. stirringstirred for 30 min at rt
  5. filtrationSuction filtration

Sources & evidence

ORD record
ord-71457f8d28fa4aadab4924059ce78956
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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