Acetic Anhydride → HCID 135858969, compound

HRID 1920675Notes

Reaction equation

[OH:1][C:2]1[C:11]([CH:12]=[N:13]O)=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:15])=[N:9]2)=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.[OH-].[Na+]>>[OH:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:15])=[N:9]2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 14798Sodium Hydroxide

HCID 136360483HCID 136360483, compound

Product 1

HCID 135858969HCID 135858969, compoundYield 60%

Conditions

Temperature: 144 °C

Procedure

Referring to FIG. 19, compound 7 (0.160 g, 0.792 mmol) was added to acetic anhydride (3.5 mL) and the resulting mixture was stirred at 144° C. under nitrogen atmosphere for 7.5 h. Concentrated NaOH solution (50%) was added to the mixture slowly with stirring until the reaction reached pH 12. The solvent was evaporated and the resulting dark brown residue was purified by column chromatography (1:1 EtOAc/hexane) to yield 5b (0.0874 g, 0.475 mmol, 60%) as a yellow solid: 1H NMR (acetone-d6) δ 8.20 (1H, J=8.0 Hz), 8.04 (1H, d, J=8.8 Hz), 7.37 (1H, d, J=8.4 Hz), 7.36 (1H, d, J=9.2 Hz), 2.69 (3H, s); 13C NMR (acetone-d6) δ 163.1, 161.7, 149.1, 136.6, 133.9, 121.0, 117.3, 114.8, 95.7, 24.7; FTIR (neat) 3111, 2922, 2229, 1620, 1577, 1508, 1446, 1342, 1271, 1143, 844 cm−1; MS (ESI) m/z calculated for (C11H8N2O+H)+ 185, found 185; HRMS (ESI) m/z calculated for (C11H8N2O+H)+ 185.0716, found 185.0766.

Workup

stirringwith stirring until the reaction
customThe solvent was evaporated
customthe resulting dark brown residue was purified by column chromatography (1:1 EtOAc/hexane)

Sources & evidence

ORD record: ord-e707d1f7ef504799987e56c6e373f9f0
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173620B2

Reaction notes

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