Oxalyl chloride → 2-Oxo-(5-phenoxy-1H-indol-3-yl)acetyl chloride

HRID 1371891

Reaction equation

HRID 1371891 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](Cl)(=[O:21])[C:18]([Cl:20])=[O:19]>CCOCC>[O:21]=[C:17]([C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)[NH:13][CH:12]=1)[C:18]([Cl:20])=[O:19]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 112412535-phenoxy-1H-indole

Product 1

HCID 210714422-Oxo-(5-phenoxy-1H-indol-3-yl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Combine 5-phenoxy-indole (1.57 g, 7.5 mmol) and anhydrous ether (35 mL) and add oxalyl chloride (1.07 g, 8.25 mmol) in 8 mL ether. A precipitate forms. Stir the reaction over night. Collect the precipitate, dry in vacuo, to give the title compound: 1H NMR (300 MHz, DMSO-d6) 6.99–7.15 (m, 4H), 7.37–7.42 (m, 2H), 7.60 (d, 1H, J=8.7 Hz), 7.75 (d, 1H, J=2.4 Hz), 8.47 (d, 1H, J=3.2 Hz), 12.49, (br, 1H).

Workup

  1. customthe reaction over night
  2. customCollect the precipitate
  3. customdry in vacuo

Sources & evidence

ORD record
ord-979f248b556d45799ea54eb7de16db03
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Linked notes

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