Hydrochloric Acid → 4-(2,3-Dihydro-indol-1-yl)-4-oxo-butyric acid

HRID 705522Notes

Reaction equation

HRID 705522 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1.Cl>N1C=CC=CC=1>[N:1]1([C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 10328Indoline

Product 1

HCID 7304294-(2,3-Dihydro-indol-1-yl)-4-oxo-butyric acidYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The procedure was modified from the reported one. In a 20 mL microwave reaction tube equipped with a magnetic stirring bar, indoline (1.196 g, 10 mmol), succinic anhydride (1.004 g, 10 mmol) and pyridine (8 mL) was mixed at room temperature. The tube was capped and irradiated in the microwave reactor (Biotage Initiator I) at 90° C. for 20 minutes. The reaction mixture was acidified to pH=1 using 2 M HCl. The resulting precipitate was filtered, washed with water and dried under high vacuum to afford light pink solid product (1.849 g, 92%). 1H NMR (400 MHz, CDCl3) d 8.19 (d, 1H, J=8.5 Hz), 7.18 (m, 2H), 7.03 (t, 1H, J=7.4 Hz), 4.08 (t, 2H, J=8.4 Hz), 3.22 (t, 2H, J=8.4 Hz), 2.78 (m, 4H).

Workup

  1. customIn a 20 mL microwave reaction tube equipped with a magnetic stirring bar
  2. customThe tube was capped
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-95f419ea3ca645a9893b764abaae0a91
Source dataset
uspto-grants-2015_11
Patent number
US09174969B2

Reaction notes

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