Hydrochloric Acid → 4-(AMINOMETHYL)-3-METHOXYBENZONITRILE

HRID 1584093Notes

Reaction equation

HRID 1584093 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=2[O:18][CH3:19])C(=O)C2=CC=CC=C12.Cl>C1COCC1.CC(OC)(C)C>[NH2:8][CH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=1[O:18][CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 22476088HCID 22476088, compound

Product 1

HCID 184240904-(AMINOMETHYL)-3-METHOXYBENZONITRILEYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

10.6 ml of hydrazine hydrate were added to 21.2 g (73 mmol) of 4-phthalimidomethyl-3-methoxybenzonitrile dissolved in 290 ml of THF, and the mixture was stirred at room temperature for 20 h. Then 180 ml of 2H [sic] HCl were added dropwise and, after 1.5 h, the solvent was completely stripped off. The residue was taken up in MTBE, extracted with 1N HCl, adjusted to pH 9-10 with 2N NaOH and extracted with methylene chloride. 8.0 g (68%) of product were obtained. 1H-NMR (DMSO-d6 ; δ in ppm): 7.55 (dd, 1H); 7.40 (dd, 1H; 7.37 (d, 1); 3.85 (s, 3H); 3.70 (s, 2H); 2.5-1.6 (NH2).

Workup

  1. extractionextracted with 1N HCl
  2. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-a4774b47eb2f41e989a25f43628557d8
Source dataset
uspto-grants-1999_08
Patent number
US05932567

Reaction notes

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