Hydrazine, dihydrochloride → HCID 178419301, compound

HRID 1799879Notes

Reaction equation

HRID 1799879 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=O)/[C:10](=[CH:13]/[N:14](C)C)/[CH2:9][CH2:8][O:7][C:6]=2[CH:17]=1.Cl.Cl.[NH2:20]N>C(O)(C)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[C:10]([CH2:9][CH2:8][O:7][C:6]=2[CH:17]=1)=[CH:13][NH:14][N:20]=3

Participants

5

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 58204579HCID 58204579, compound

Product 1

HCID 178419301HCID 178419301, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 8-bromo-4-[1-dimethylamino-meth-(E)-ylidene]-3,4-dihydro-2H-benzo[b]-oxepin-5-one (5.32 g, 17.9 mmol) in isopropyl alcohol (50 mL) was added powdered hydrazine dihydrochloride (3.77 g, 35.9 mmol) at room temperature, then the mixture stirred for 2 h. The reaction mixture was diluted with water (20 mL) and then heated at 100° C. for 2 h before cooling to room temperature. The reaction mixture was concentrated in vacuo to remove the volatile solvent. The resulting suspension was filtered and the filtrate washed with water and dried under vacuum at 40° C. to yield 8-Bromo-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene as a pale yellow solid (4.28 g, 90%). 1H NMR δ (ppm) (DMSO-d): 8.07 (1H, d, J=8.52 Hz), 7.64 (1H, s), 7.30-7.24 (1H, m), 7.21 (1H, d, J=2.07 Hz), 4.24 (2H, dd, J=5.63, 4.50 Hz), 3.00 (2H, t, J=5.09 Hz).

Workup

  1. temperaturebefore cooling to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove the volatile solvent
  4. filtrationThe resulting suspension was filtered
  5. washthe filtrate washed with water
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-7c7e77e24b944ec8b47d5fc680dfbebf
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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