Acetaminophen → HCID 58167965, compound

HRID 1029116Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[OH:17][C:18]1[CH:23]=[CH:22][C:21](NC(=O)C)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].C[N:35]([CH:37]=[O:38])C>CO>[O:12]=[C:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]2[C:8](=[N:9][CH:10]=[CH:11][C:2]=2[O:17][C:18]2[CH:19]=[CH:20][C:21]([C:37]([NH2:35])=[O:38])=[CH:22][CH:23]=2)[NH:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), N-(4-hydroxyphenyl)acetamide (59 mg, 0.39 mmol), and potassium carbonate (90 mg, 0.65 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, and filtered through a membrane. The crude product was purified via prep-LC-MS to provide 135 (3 mg, 7% yield) as a solid. LC-MS (M+H=346, obsd.=346). 1H NMR (400 MHz, d6-DMSO): δ 12.14 (s, 1H), 10.15 (s, 1H), 9.08 (d, 1H), 8.42 (d, 1H), 8.29 (d, 1H), 7.88 (t, 1H), 7.73 (m, 3H), 7.28 (d, 2H), 6.52 (d, 1H), 2.09 (s, 3H).

Workup

filtrationfiltered through a membrane
customThe crude product was purified via prep-LC-MS

Sources & evidence

ORD record: ord-8d11af769c8d463493a595b484abac42
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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