Methane → 2-methoxy-6-[(N-2-aminophenyl)-amino]-8-methylquinoline

HRID 1198939Notes

Reaction equation

HRID 1198939 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([CH3:23])[CH:7]=[C:8]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:20]([O-])=O)[CH:9]=2)[N:4]=1.C>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([CH3:23])[CH:7]=[C:8]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH2:20])[CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 297MethaneHCID 198677162-methoxy-6[(N-2-nitrophenyl)-amino]-8-methylquinoline

Product 1

HCID 544931382-methoxy-6-[(N-2-aminophenyl)-amino]-8-methylquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-methoxy-6[(N-2-nitrophenyl)-amino]-8-methylquinoline (0.2 g) in absolute ethanol (20 cm3) was hydrogenated at 60° and 60 p.s.i. (4.13×105Pa) pressure over 10% palladised charcoal (0.03 g) for 4 hours. The cooled solution was then filtered through "Solkafloc" (Trade Mark for a cellulose-based filtering aid), evaporated to dryness in vacuo, characterised spectroscopically and used directly in Preparation 16 without further purification.

Workup

  1. customwas hydrogenated at 60°
  2. filtrationThe cooled solution was then filtered through "Solkafloc" (Trade Mark for a cellulose-
  3. filtrationbased filtering aid),
  4. customevaporated to dryness in vacuo
  5. customused directly in Preparation 16 without further purification

Sources & evidence

ORD record
ord-d0df142ccb79462fafa1647de8069b65
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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