Propyl isocyanate → HCID 59300866, compound

HRID 2235446Notes

Reaction equation

HRID 2235446 reaction equation
[CH3:1][C:2]1([CH3:26])[C:10]2[C:5](=[CH:6][C:7]([N+:22]([O-])=O)=[C:8]([NH:11][C:12](=O)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[NH:4][C:3]1=[O:25].[CH2:27]([N:30]=[C:31]=[O:32])[CH2:28][CH3:29]>C1(C)C=CC=CC=1>[CH2:27]([NH:30][C:31]([N:4]1[C:5]2[CH:6]=[C:7]3[N:22]=[C:12]([C:13]4[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=4)[NH:11][C:8]3=[CH:9][C:10]=2[C:2]([CH3:26])([CH3:1])[C:3]1=[O:25])=[O:32])[CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 23092680HCID 23092680, compound

Product 1

HCID 59300866HCID 59300866, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-4-methoxy-benzamide (200 mg) and propyl isocyanate (59 μl) in dry toluene (2 ml) is stirred in a microwave apparatus at 150° C. for 900 s. The resulting solid is collected by filtration, dissolved in acetic acid (3 ml) and iron (200 mg; powder) is added and the mixture is again stirred in a microwave apparatus at 150° C. for 900 s to achieve reduction of the nitro function and ring closure. The mixture is filtered and concentrated in vacuo. The desired compound (65 mg) is obtained by preparative RP-HPLC.

Workup

  1. filtrationThe resulting solid is collected by filtration
  2. dissolutiondissolved in acetic acid (3 ml)
  3. additioniron (200 mg; powder) is added
  4. filtrationThe mixture is filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0e78fee54334c428dfd11e04867e3e9
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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