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

HRID 2184235Notes

Reaction equation

HRID 2184235 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 RT for 20 h. Then 180 ml of 2N 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 DCM. 8.0 g (68%) of the product were obtained. 1H-NMR (DMSO-d6; δ in ppm): 7.55 (dd, 1H); 7.40 (dd, 1H); 7.37 (d, 1H); 3.85 (s, 3H); 3.70 (s, 2H); 2.5-1.6 (NH2).

Workup

  1. extractionextracted with 1N HCl
  2. extractionextracted with DCM

Sources & evidence

ORD record
ord-bbabbc99ea714e8a9b97bcca654810f1
Source dataset
uspto-grants-2005_05
Patent number
US06900319B2

Reaction notes

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