Methanol → HCID 49856750, compound

HRID 1520759Notes

Reaction equation

HRID 1520759 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:14]2[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=2[C:12]2[C:7](=[C:8]3[CH:27]=[CH:26][CH:25]=[CH:24][C:9]3=[N:10][C:11]=2Cl)[N:6]=1.[CH3:28][OH:29]>>[CH3:1][O:2][C:5]1[C:14]2[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=2[C:12]2[C:7](=[C:8]3[CH:27]=[CH:26][CH:25]=[CH:24][C:9]3=[N:10][C:11]=2[O:29][CH3:28])[N:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 49856749HCID 49856749, compound

Product 1

HCID 49856750HCID 49856750, compound

Procedure

Sodium methoxide (63 mg, 1.17 mmol) and 33 (70 mg, 0.2 mmol) were mixed in methanol (10 mL). The mixture was heated to reflux for 10 h. The reaction mixture was cooled to room temperature and ice-cold water (10 mL) was added. The precipitated white amorphous solid (50 mg, 71%) was collected by filtration: mp 173-175° C. IR (KBr) 1650, 1610, 1590, 1515 cm−1; 1H NMR (500 MHz, DMSO-d6) δ 8.80 (d, J=7.2 Hz, 1 H), 8.57 (s, 1 H), 7.78 (d, J=7.8 Hz, 1 H), 7.70 (t, J=7.3 Hz, 1 H), 7.59-7.45 (m, 2 H), 4.24 (s, 3 H), 4.19 (s, 3 H), 3.95 (s, 3 H), 3.91 (s, 3 H); 13C NMR (126 MHz, CDCl3) δ 160.78, 159.51, 153.11, 149.48, 146.29, 143.82, 129.96, 129.49, 126.60, 124.42, 124.34, 123.50, 114.22, 107.61, 105.68, 103.90, 55.82, 55.72, 54.24, 53.95; positive ESIMS m/z (rel intensity) 351 (MH+, 100). Anal. Calcd for C20H18N2O4.0.6H2O: C, 66.51; H, 5.36; N, 7.76. Found: C, 66.41; H, 5.08; N, 7.54.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 10 h
  3. filtrationThe precipitated white amorphous solid (50 mg, 71%) was collected by filtration

Sources & evidence

ORD record
ord-a0603cf0e4db48d2bcb0402e2eaeb6e8
Source dataset
uspto-grants-2015_07
Patent number
US09073920B2

Reaction notes

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