Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → HCID 5377737, compound

HRID 1752027Notes

Reaction equation

HRID 1752027 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.[CH3:18][C:19](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:20]>N1C=CC=CC=1>[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:6][CH:7]=1)(=[O:20])[CH3:18]

Participants

4

Reactant 2

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 6176231HCID 6176231, compound

Product 1

HCID 5377737HCID 5377737, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ketone 30t was prepared from aniline 30r (0.045 mmol.), treated with 500 μL of a solution 40% anhydrous acetic in pyridine at room temperature for 2 hours. The solvent was removed and the product was precipitated with 1N NaOH. The solid was washed with water and obtained as a yellow solid (77% yield). mp 191-193° C. 1H NMR (CDCl3) δ 9.21 (s, 1H), 8.79 (s, 1H), 8.27 (dt, 1H, J=7.9 Hz, 1.8 Hz), 7.78 (d, 1H, J=15.7 Hz), 7.59 (s, 4H), 7.39 (m, 3H), 2.19 (s, 3H). 13C NMR (CDCl3) δ 189.42, 169.02, 153.39, 149.99, 145.83, 140.87, 136.29, 133.97, 130.08, 124.07, 120.50, 120.03, 25.11. HRMS (FAB) calcd for C16H15N2O2 ([M+H]+): 267.1128. found 267.1141.

Workup

  1. customThe solvent was removed
  2. customthe product was precipitated with 1N NaOH
  3. washThe solid was washed with water

Sources & evidence

ORD record
ord-8e0536efc4044d9fb72b90b0f6efbd84
Source dataset
uspto-grants-2015_10
Patent number
US09162991B2

Reaction notes

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