Sodium Carbonate → HCID 66803379, compound

HRID 711390Notes

Reaction equation

HRID 711390 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][C:6]([N+:12]([O-])=O)=[C:5]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[CH:18][CH:17]=1.O.O.Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O>[NH2:12][C:6]1[N:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([CH3:25])([CH3:26])[C:23]#[N:24])=[CH:20][CH:21]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 61436Stannous chloride dihydrateHCID 66803411HCID 66803411, compound

Product 1

HCID 66803379HCID 66803379, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under N2, an orange solution of 2-(4-(6-bromo-3-nitrocinnolin-4-ylamino)phenyl)-2-methylpropanenitrile (2.5 g, 6.06 mmol) and SnCl2.2H2O (5.21 g, 24.26 mmol) in EtOAc (50 mL) was heated at 45° C. for 3 h. After cooling to r.t., the pH of the mixture was adjusted to 8 with saturated Na2CO3. The mixture was filtered through a Buchner funnel, and the filtrate was collected and concentrated to give 2-(4-(3-amino-6-bromocinnolin-4-ylamino)phenyl)-2-methylpropanenitrile (1.6 g, yield 69%). MS (m/z): 384 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a Buchner funnel
  2. customthe filtrate was collected
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-88601e5288844ef98915100f1afe78fb
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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