Phenylglycine nitrile → 1H-Indazole-3-carbonitrile

HRID 549067

Reaction equation

HRID 549067 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6].[N:11]([O-])=O.[Na+]>Cl>[C:5]([C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][N:11]=1)#[N:6]

Participants

4

Reactant 2

HCID 76307Phenylglycine nitrileHCID 23668193Sodium Nitrite

Product 1

HCID 4375561H-Indazole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of o-aminobenzyl cyanide (0.5 g) in aqueous hydrochloric acid 1N (9.6 mL), was treated with a solution of aqueous sodium nitrite 1N (3.85 mL). After stirring at room temperature for 15 minutes, the reaction mixture was filtered. The solid was recrystallised from ethanol to give the title compound (0.4 g) as a yellow solid, m.p. 138-140° C. 1H NMR [(CD3)2SO]: δ 7.89 (d, 1H, J=7.7 Hz); 7.76 (d, 1H, J=7.9 Hz); 7.48 (t, 1H); 7.41 (t, 1H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customThe solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-99b2645688ee40448ec16adfb554ec7a
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Linked notes

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