Hydrochloric Acid → 2-Nitro-5-(3-phenoxypropoxy)-indan-1,3-dione

HRID 1706465Notes

Reaction equation

[O:1]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[CH2:16][C:15]2=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:23]([O-])([OH:25])=[O:24].Cl>CCOCC>[N+:23]([CH:16]1[C:15](=[O:22])[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([O:11][CH2:10][CH2:9][CH2:8][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:13]=2)[C:17]1=[O:21])([O-:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 5-(3-phenoxypropoxy)-indan-1,3-dione (0.296 gm, 0.001 mole) was suspended in dry ether (10 ml) and cooled to 0° C. The stirred mixture was treated with fuming nitric acid (1 ml) added dropwise over 15 mins and stirred in the ice bath for 1 hr. The mixture was then stirred at r.t. for a further 11/2 hrs. During this time all the solid dissolved leaving a deep yellow solution. Dilute hydrochloric acid (20 ml) was added and the ether evaporated in vacuo. A yellow gum formed which solidfied on scratching to give 0.25 gm of yellow solid which had mp 77°-79° C.(d). (73%). (Found; C, 60.71; H, 4.58; N, 3.66; C18H15NO6.0.75H2O requires; C, 60.92; H, 4.69; N, 3.95%).

Workup

additionadded dropwise over 15 mins
dissolutionDuring this time all the solid dissolved
customleaving a deep yellow solution
customthe ether evaporated in vacuo
customA yellow gum formed which

Sources & evidence

ORD record: ord-5d81176766914e2ead890e16b6dd5f7b
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04207335

Reaction notes

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