O-Toluidine → HCID 22180106, compound

HRID 1795887Notes

Reaction equation

HRID 1795887 reaction equation
[C:1](=[O:29])([O:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([CH2:23][C:24]([OH:26])=[O:25])=[C:16](F)[C:15]=1[F:28])[O:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[NH2:30][C:31]1[C:32]([CH3:37])=[CH:33][CH:34]=[CH:35][CH:36]=1>C(OCC)C>[C:1](=[O:29])([O:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([CH2:23][C:24]([OH:26])=[O:25])=[C:16]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])[C:15]=1[F:28])[O:2][C:3]12[CH2:10][CH:9]3[CH2:11][CH:5]([CH2:6][CH:7]([CH2:8]3)[CH2:12]1)[CH2:4]2

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 22180099HCID 22180099, compound

Product 1

HCID 22180106HCID 22180106, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

The compound 1-adamantyl 4-carboxymethyl-2,3-difluoro-6-nitrophenyl carbonate is dissolved in excess ortho-toluidine. The reaction mixture is stirred at 200° C. for 6 hours. The mixture is allowed to cool and is dissolved in diethyl ether. The organic phase is washed with dilute aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and brine, is dried (MgSO4), and is concentrated in vacuo to afford the desired product. The product is purified by flash chromatography as necessary.

Workup

  1. temperatureto cool
  2. washThe organic phase is washed with dilute aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and brine
  3. dry with materialis dried (MgSO4)
  4. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-aad06831eb2c4e4b97b913f05f429aa8
Source dataset
uspto-grants-2006_04
Patent number
US07030119B1

Reaction notes

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