2-Tetralone → HCID 58156756, compound

HRID 2172149Notes

Reaction equation

HRID 2172149 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=O.[CH3:12]OC(OC)N(C)C.[NH:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26])[NH2:21]>O>[CH:12]1[C:1]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:4][CH2:3][C:2]=2[N:20]([C:22]2[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=2)[C:25]([OH:27])=[O:26])[N:21]=1

Participants

5

Reactant 3

HCID 682662-TetraloneHCID 78373Dimethylformamide dimethyl acetalHCID 27365213-Hydrazinobenzoic acid

Product 1

HCID 58156756HCID 58156756, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-tetralone (2.00 mL, 14.7 mmol) and dimethylformamide dimethyl acetal (2.10 mL, 15.0 mmol) is heated to reflux for 14 h. The mixture is cooled and evaporated, and approximately half of the residue is dissolved in acetic acid (10 mL) and treated with 3-hydrazinobenzoic acid (750 mL, 4.93 mmol). The solution is heated to reflux for 12 h, then cooled and poured into water (100 mL). The resulting precipitate is collected by filtration, washed with water, and evaporated under high vacuum to afford the title compound (900 mg, 3.10 mmol, 63%) as a tan solid, m.p. 273-275° C. 1H NMR (300 MHz, DMSO-d6): δ 13.30 (1H, br), 8.15 (1H, s), 8.10 (1H, t, J=1.9 Hz), 7.95 (1H, dt, J=7.6, 1.3 Hz), 7.82 (1H, ddd, J=8.0, 2.2, 1.0 Hz), 7.66 (1H, t, J=7.9 Hz), 7.53 (1H, dd, J=7.6, 1.2 Hz), 7.26-7.22 (2H, m), 7.10 (1H, dt, J=7.3, 1.2 Hz), 3.05-3.02 (2H, m), 3.00-2.87 (2H, m). MS (ES+): m/e 292 (21), 291 (100). MS (ES−): m/e 290 (20), 289 (100).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 14 h
  3. temperatureThe mixture is cooled
  4. customevaporated
  5. dissolutionapproximately half of the residue is dissolved in acetic acid (10 mL)
  6. temperatureThe solution is heated
  7. temperatureto reflux for 12 h
  8. temperaturecooled
  9. filtrationThe resulting precipitate is collected by filtration
  10. washwashed with water
  11. customevaporated under high vacuum

Sources & evidence

ORD record
ord-4c31e082087043be96f64be21bb080e2
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

Loading…