tert-butyl N-(3-aminophenyl)carbamate → 5-(3-Aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

HRID 1049717Notes

Reaction equation

HRID 1049717 reaction equation
FC(F)(F)S(OC1C=CC2C(=CC=CC=2)C=1[N+]([O-])=O)(=O)=O.C(OC(=O)NC1C=CC=C(N)C=1)(C)(C)C.CC1C(C)=CC=CC=1C(NC1C=CC(N2C(=O)CC(=O)NC3C4C(C=CC2=3)=CC=CC=4)=CC=1F)=O.[NH2:72][CH2:73][C:74]1C=[CH:78][C:77]([N:80]2[C:86](=[O:87])[CH2:85][C:84](=[O:88])[NH:83][C:82]3[C:89]4[C:94]([CH:95]=[CH:96][C:81]2=3)=[CH:93][CH:92]=[CH:91][CH:90]=4)=[CH:76][CH:75]=1>>[NH2:72][C:73]1[CH:78]=[C:77]([N:80]2[C:86](=[O:87])[CH2:85][C:84](=[O:88])[NH:83][C:82]3[C:89]4[C:94]([CH:95]=[CH:96][C:81]2=3)=[CH:93][CH:92]=[CH:91][CH:90]=4)[CH:76]=[CH:75][CH:74]=1

Participants

5

Reactant 4

HCID 12877220tert-butyl N-(3-aminophenyl)carbamateHCID 147652731-Nitronaphthalen-2-yl triflateHCID 117699184HCID 117699184, compoundHCID 117699239HCID 117699239, compound

Product 1

HCID 1176991925-(3-Aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dioneYield 17%

Procedure

By using 1-nitro-2-naphthyl trifluoromethanesulfonate (5.94 g, 18.5 mmol), and tert-butyl(3-aminophenyl)carbamate, the title compound (1.02 g, yield 17%) was obtained as brown crystals in the same manner as that of Example 1, (1), (2) and (3).

Sources & evidence

ORD record
ord-2aed8a42787944fe9afd600a1a77c6c3
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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