Hydrochloric Acid → HCID 136331260, compound

HRID 523870Notes

Reaction equation

HRID 523870 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([OH:15])[CH3:14].[ClH:16]>O1CCOCC1>[ClH:16].[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[NH:7])[O:15][CH2:13][CH3:14])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 136331260HCID 136331260, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of 4-hydroxy-3-nitrobenzonitrile 33 (5.2 g, 32 mmol) in a solution of abs. ethanol (250 ml) and dioxane (40 ml) was cooled in an ice bath as dry HCl gas was bubbled through it for 1 hr. The mixture was stirred overnight at room temperature and the resulting precipitate was collected, washed with ether and dried to give 6.2 g (79%) of the imidate ester HCl 34. 1H NMR (600 MHz, DMSO-d6) δ 11.8 (br s, 1H), 8.64 (s, 1H), 8.21 (d, 1H, J=9 Hz), 7.38 (d, 1H, J=9 Hz), 4.57 (q, 2H, J=7.2 Hz), 1.47 (t, 3H, J=7.2 Hz).

Workup

  1. customwas bubbled through it for 1 hr
  2. customthe resulting precipitate was collected
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-6962785fef2f434787df54bcdf568de9
Source dataset
uspto-grants-2016_05
Patent number
US09340505B2

Reaction notes

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