Ethanol → HCID 10200859, compound

HRID 1278799Notes

Reaction equation

HRID 1278799 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([N+:24]([O-])=O)[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.NN.C(O)C>O>[NH2:24][C:19]1[CH:18]=[C:17]([C:9]2[C:10]3[C:14]([CH3:15])=[C:13]([CH3:16])[S:12][C:11]=3[C:2]([Br:1])=[C:3]3[C:8]=2[CH:7]=[CH:6][CH:5]=[CH:4]3)[CH:22]=[CH:21][C:20]=1[OH:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 22665455HCID 22665455, compound

Product 1

HCID 10200859HCID 10200859, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Using a procedure similar to Tet. Lett. 1990, 1181-1182, Montmorillinite K10 clay (425 mg) was added to a solution of 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-nitro-phenol (0.608 g, 1.42 mmol), anhydrous hydrazine (0.276 μL, 8.95 mmol) and ethanol (4.2 mL) and the suspension was heated at 85° C. for 30 min. The reaction mixture was cooled to room temperature, added to water and extracted with ether. The ether was dried and concentrated to provide the title compound as a white solid (0.576 g, 100%): mp 173-175° C.: NMR (DMSO-d6); δ 9.26 (s, 1H), 8.14 (dd, J=8, 1 Hz, 1H), 7.63-7.58 (m, 2 H), 7.42 (ddd, J=8, 6, 1 Hz, 1H), 6.78 (d, J=8 Hz, 1H), 6.54 (d, J=2 Hz, 1H), 6.35 (dd, J=8, 2 Hz, 1H), 4.67 (broad s, 2H), 2.42 (s, 3H), 1.69 (s, 3H); MS (+FAB): 1 bromine isotope pattern 398 (30%, M+H), 400 (30%, M+H); Anal. Calc. for C20H16BrNOS: C, 60.31, H, 4.05, N, 3.52; Found: C, 61.36, H, 4.08, N, 3.25.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ether
  3. dry with materialThe ether was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9b2f37b9b72243b69285f4ef312927bb
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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