Sodium Cyanide → 2-Cyanophenylacetic acid

HRID 1196572노트

반응식

HRID 1196572 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 877552-Cyanophenylacetic acid

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 14798Sodium Hydroxide용매

실험 절차

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).

출처 및 근거

ORD 기록
ord-9c46674a505443329b8f608854c3f72f
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05114940

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