Phenylglycine nitrile → 1H-Indazole-3-carbonitrile

HRID 1835231Notes

Reaction equation

HRID 1835231 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=7.7Hz); 7.76 (d, 1H, J=7.9Hz); 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-2368d8c4a8d34c1dbefa129e7d2119f6
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

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