NSC359701 → HCID 58667806, compound

HRID 643229Notes

Reaction equation

HRID 643229 reaction equation
C(NC1C(=O)OC2C(C=1)=CC(N)=CC=2)(=O)C.[N+:17]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][C:25](=[O:30])[C:24]([C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-])=O)=[CH:33][CH:32]=1)=[CH:23]2)([O-])=O.[BH4-].[Na+]>[Pd].O.CO>[NH2:17][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][C:25](=[O:30])[C:24]([C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1)=[CH:23]2

Participants

7

Reactant 3

HCID 338232NSC359701HCID 4311764Sodium borohydrideHCID 49052456-Nitro-3-p-nitrophenylchromen-2-one2×

Product 1

HCID 58667806HCID 58667806, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Following the same protocol used to obtain diamine 2, palladium on carbon (10% water) (0.322 g, 1/10th of the mass of 11) and a solution of sodium borohydride (1.21 g, 32.9 mmol) in water (22.6 mL) were used to reduce a suspension of compound 11 (4.03 g, 12.9 mmol) in methanol (775 mL). In this way, compound 12 (2.04 g, 8.1 mmol) was obtained as a yellow solid in 63% yield. FTIR (KBr) (cm−1): 3180, 3120, 1700, 1610, 850. 1H-NMR (DMSO-d6): δ (ppm) 7.84 (s, 1H), 7.46 (d, J=8.5 Hz, 2H), 7.08 (d, J=8.6 Hz, 1H), 6.79 (d, J=8.5 Hz, 1H), 6.77 (s, 1H), 6.60 (d, J=7.8 Hz, 2H), 5.32 (ds, 3H), 5.15 (ds, 3H). 13C-NMR (DMSO-d6): δ (ppm) 163.34, 150.20, 146.43, 145.43, 137.99, 130.38, 127.88, 123.18, 11.33, 118.85, 116.94, 114.39, 111.04. HRMS: expected, 252.089878; found, 252.089846. Elemental analysis for C15H12N2O2: expected: C, 71.42; H, 4.79; N, 11.10; found: C, 71.30; H, 4.58; N, 10.92

Sources & evidence

ORD record
ord-fe69758852fc4e2e8920d19934056c08
Source dataset
uspto-grants-2010_04
Patent number
US07700375B2

Reaction notes

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