Oxalyl chloride → 4-(4-tert-Butoxycarbonylaminophenyl)-1,4-dihydrobenzo[f]quinoxaline-2,3-dione

HRID 1186746Notes

Reaction equation

HRID 1186746 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:15][CH:14]=1.[C:27](Cl)(=[O:31])[C:28](Cl)=[O:29]>>[C:23]([O:22][C:20]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:3]3[CH:4]=[CH:5][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:2]=3[NH:1][C:28](=[O:29])[C:27]2=[O:31])=[CH:14][CH:15]=1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 65578Oxalyl chlorideHCID 86690020tert-Butyl (4-((1-aminonaphthalen-2-yl)amino)phenyl)carbamate

Product 1

HCID 866900194-(4-tert-Butoxycarbonylaminophenyl)-1,4-dihydrobenzo[f]quinoxaline-2,3-dioneYield 38%

Procedure

1-Amino-2-(4-tertbutoxycarbonylaminophenyl)aminonaphthalene (700 mg, 2.0 mmol) and oxalyl chloride (330 mg, 2.6 mmol) were used in a process similar to Example 1(3) to give the titled compound (304 mg, yield 38%).

Sources & evidence

ORD record
ord-58b4f474b99d410f986cb1dd6483c9de
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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