Phenylglycine nitrile → 1H-Indazole-3-carbonitrile

HRID 1765612Notes

Reaction equation

HRID 1765612 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-f08235661cfa41e59892e7e57990ba45
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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