Acetic Anhydride → HCID 9816181, compound

HRID 992559Notes

Reaction equation

HRID 992559 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([CH2:14][OH:15])[N:2]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([O:15][CH2:14][C:3]1[N:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3)(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 53533383-Hydroxymethyl-beta-carboline

Product 1

HCID 9816181HCID 9816181, compound

Procedure

A suspension of 9H-β-carboline-3-methanol (99 mg, 0.50 mmol) in acetic anhydride (10 mL) was stirred for 4 hours at room temperature, during which time the starting material dissolved. Removal of the acetic anhydride in vacuo afforded a tan solid (122 mg). Purification by flash chromatography on silica gel with ethyl acetate as the eluent afforded 82 mg (68%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ9.49 (s, 1H), 8.99 (s, 1H), 8.13 (d, J=8.0, 1H), 8.07 (s, 1H), 7.56-7.61 (m, 2H), 7.26-7.34 (m, 1H), 5.43 (s, 2H), 2.15 (s, 3H). LRMS calcd for C14H12N2O2 (M+H) 241, found 241.0.

Workup

  1. dissolutiondissolved
  2. customRemoval of the acetic anhydride in vacuo

Sources & evidence

ORD record
ord-b58167142e7e4259a20b1411fe19676d
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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