Hydrochloric Acid → HCID 21556219, compound

HRID 267374Notes

Reaction equation

NC1C=CC=CC=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:25])[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[CH:10][CH:9]=1.Cl.[N:27]([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[C:37]1([CH3:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O>[C:43]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:25])[C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])=[CH:10][CH:9]=1)#[N:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To 29.4 g. (0.1 moles) of benzyl 2'-amino-4-biphenylylglycolate in 35 ml. of 28% hydrochloric acid and 100 ml. of cracked ice to maintain the temperature at 0°C is added a solution of 7.1 g (0.102 moles) of sodium nitrite in 20 ml. of water. The reaction mixture is then neutralized with sodium carbonate. This diazonium mixture is added to a cuprous cyanide solution (prepared from 31.5 g. of copper sulfate and 16.2 of sodium cyanide in 75 ml. of water). 250 ml. of toluene is also added and the mixture is stirred for 1/2 hour. The reaction is then allowed to stir an additional 2 hours while warming gradually to 50°C. This is then cooled and the toluene separated, dried over sodium sulfate and evaporated to dryness to obtain benzyl 2'-cyano-4-biphenylylglycolate.

Workup

stirringto stir an additional 2 hours
temperaturewhile warming gradually to 50°C
temperatureThis is then cooled
customthe toluene separated
dry with materialdried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-62f32f61fd22439ca3874b43c0080364
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03941821

Reaction notes

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