Indan-5-amine → 2-Bromo-N-indan-5-yl-5-nitro-benzamide

HRID 1531276Notes

Reaction equation

HRID 1531276 reaction equation
C1(S(N[CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:20]C(C4C(C5C=CC(C(F)(F)F)=CC=5)=CC=CC=4)=O)[CH:17]=3)[CH2:12]2)(=O)=O)C=CC=CC=1.[Br:39][C:40]1[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][C:41]=1[C:42](Cl)=[O:43].NC1C=C2C(=CC=1)CCC2>>[Br:39][C:40]1[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][C:41]=1[C:42]([NH:20][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:19]2)=[O:43]

Participants

4

Reactant 3

HCID 90496Indan-5-amineHCID 98933624''-Trifluoromethyl-biphenyl-2-carboxylic acid (2-benzenesulfonylamino-indan-5-yl)-amideHCID 114710722-Bromo-5-nitrobenzoyl chloride

Product 1

HCID 212533662-Bromo-N-indan-5-yl-5-nitro-benzamide

Procedure

2-Bromo-N-indan-5-yl-5-nitro-benzamide is prepared similarly to the title E compound of Example 1 using the title A compound, 2-bromo-5-nitrobenzoyl chloride (1.07 g, 4.06 mmol) and 5-aminoindan (0.54 g, 4.06 mmol). 1H NMR (DMSO-d6, 300 MHz): δ 10.52 (1H, s), 8.34 (1H, d), 8.21 (1H, dd), 8.03 (1H, d), 7.60 (1H, s), 7.38 (1H, d), 7.19 (1H, d), 2.85 (4H, m), 2.02 (2H, m).

Sources & evidence

ORD record
ord-a935927ef9414c679508a4e87a2ff010
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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