Ammonium Hydroxide → 7-Hydroxy-4-(1H-indazol-6-ylamino)-quinoline-3-carbonitrile

HRID 1595792Notes

Reaction equation

HRID 1595792 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:21]C)=[CH:18][CH:19]=4)[N:14]=[CH:13][C:12]=3[C:23]#[N:24])[CH:8]=2)[CH:3]=[N:2]1.Cl.N1C=CC=CC=1.[NH4+].[OH-]>>[OH:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([NH:10][C:7]3[CH:8]=[C:9]4[C:4]([CH:3]=[N:2][NH:1]4)=[CH:5][CH:6]=3)=[C:12]([C:23]#[N:24])[CH:13]=[N:14]2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 99666624-(1H-indazol-6-ylamino)-7-methoxy-quinoline-3-carbonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 1354182087-Hydroxy-4-(1H-indazol-6-ylamino)-quinoline-3-carbonitrileYield 99.8%

Conditions

Temperature
205 °C

Procedure

A reaction mixture of 1.74 g (5.52 mmol) of 4-(1H-Indazol-6-ylamino)-7-methoxy-quinoline-3-carbonitrile and 15.3 g of pyridine hydrochloride was heated at 200-210° C. for 1.5 hr. After cooling, the mixture was taken into 3% NH4OH aqueous solution. The precipitate was collected by filtration and washed with water. Drying in vacuo afforded 1.66 g (63.8%) of the product as deep brown solid, m.p.>250° C., mass (electrospray, m/e): M+H 301.9. HRCIMS: calcd 302.1042 for C17H11N5O (M+) obsd 302.1079.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-3212590ea07847fcadb33254213f5794
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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