Hydrazine hydrate (1:1) → HCID 68756246, compound

HRID 1615247Notes

Reaction equation

HRID 1615247 reaction equation
[O:1]1[CH2:5][CH2:4]O[CH:2]1[C:6]1[CH:7]=[CH:8][C:9](F)=[C:10]([CH:13]=1)[C:11]#[N:12].[OH2:15].[NH2:16][NH2:17]>C(O)CCC>[O:15]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:13]=[C:10]2[C:9](=[CH:8][CH:7]=1)[NH:17][N:16]=[C:11]2[NH2:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 55255896HCID 55255896, compound

Product 1

HCID 68756246HCID 68756246, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-(1,3-dioxolan-2-yl)-2-fluorobenzonitrile (567 mg, 3 mmol) in n-butanol (5 mL) was added hydrazine hydrate (1.47 mL, 30 mmol). The solution was heated to 110° C. for 2 h and cooled to room temperature. The solution was stirred overnight and the resulting precipitate was collected to give the title compound as a white solid (220 mg, 36%). 1H NMR (400 MHz, DMSO-d6) δ 11.44 (s, 1H), 7.78 (s, 1H), 7.28-7.26 (m, 1H), 7.21-7.19 (m, 1H), 5.72 (s, 1H), 5.37 (bs), 4.08-4.02 (m, 2H), 3.98-3.92 (m, 2H); MS ESI 206.0 [M+H]+, calcd for [C10H11N3O2+H]+ 206.1.

Workup

  1. temperaturecooled to room temperature
  2. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-2afee807625240329eede4bbc52112d2
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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