Ethanol → HCID 10277285, compound

HRID 1278800Notes

Reaction equation

HRID 1278800 reaction equation
[Br:1][C:2]1([N+]([O-])=O)[CH:7]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[S:17][C:16]=3[C:15]([Br:23])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=CC1O.[NH2:28]N.[CH2:30]([OH:32])[CH3:31]>>[NH2:28][C:31]1[CH:5]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[S:17][C:16]=3[C:15]([Br:23])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:7]=[C:2]([Br:1])[C:30]=1[OH:32]

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 22665456HCID 22665456, compound

Product 1

HCID 10277285HCID 10277285, compoundYield 66%

Conditions

Temperature
85 °C

Procedure

Using a procedure similar to Tet. Lett. 1990, 1181-1182, Montmorillinite K10 clay (1.4 g) was added to a solution of 2-bromo-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-nitro-phenol (1.2 g, 2.37 mmol), anhydrous hydrazine (1 mL) and ethanol (7.2 mL) and the suspension was heated at 85° C. for 1 h. The reaction mixture was cooled to room temperature and concentrated. The residue was twice flash chromatographed (first time, eluent: ether, second time, eluent: 4:1 petrolerum ether ethyl acetate) to provide the title compound as a white solid (0.741 g, 66%): NMR (DMSO-d6); δ 8.16 (ddd, J=8, 1, 1 Hz, 1H), 7.65-7.60 (m, 2 H), 7.47 (ddd, J=8, 6, 1 Hz, 1H), 6.65 (d, J=2 Hz, 1H), 6.57 (d, J=2 Hz, 1H), 2.43 (d, J=1 Hz, 3H), 1.73 (d, J=1 Hz, 3H); MS (EI): 2 bromine isotope pattern 475 (50%, M+H), 477 (100%, M+H), 479 (50%, M+H); Anal. Calc. for C20H15Br2NOS: C, 50.34, H, 3.17, N, 2.94. Found: C, 51.35, H, 3.35, N, 2.72.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customchromatographed (first time, eluent: ether, second time, eluent: 4:1 petrolerum ether ethyl acetate)

Sources & evidence

ORD record
ord-8977bb17ddd147dbb1838d6bd870b98e
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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