Sodium Cyanide → 2-Cyanophenylacetic acid

HRID 1196572ノート

反応式

HRID 1196572 の反応式
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-])=O.[C-:14]#[N:15].[Na+]>[Pd].[OH-].[Na+]>[C:14]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])#[N:15]

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 77337(2-Nitrophenyl)acetic acid

生成物 1

HCID 877552-Cyanophenylacetic acid

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 14798Sodium Hydroxide溶媒

実験手順

2-Nitrophenylacetic acid (ex Aldrich) (18.1 g) dissolved in 0.1M.aq.sodium hydroxide (100 ml) was subjected to catalytic hydrogenation (at 30-40 psi) over 10% palladium on charcoal (2 g) until uptake ceased. The resultant solution was subjected first to diazotisation and then reaction with sodium cyanide and cuprous cyanide according to Simchen and Hafner, Ann. Chem., 1974, 1802 to give crude 2-cyanophenylacetic acid (14.9 g). The latter was treated with phosphorous pentachloride (20.6 g) and anhydrous hydrogen chloride in di-n-butyl ether (250 ml) for 2 hours. After a further 18 hours the volatiles were removed, the residue washed with water and recrystallized from ethanol to give 1-chloro-3-hydroxy-isoquinoline (1.48 g).

出典と根拠

ORDレコード
ord-9c46674a505443329b8f608854c3f72f
出典データセット
uspto-grants-1992_05
特許番号
US05114940

反応ノート

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