Water → HCID 22040478, compound

HRID 2070336Notes

Reaction equation

HRID 2070336 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].F[C:8]1[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:12][CH:11]=[C:10]([N+:21]([O-])=O)[C:9]=1[NH2:24].O.[OH-].[Na+]>C1COCC1>[CH:20]1([N:17]2[CH2:18][CH2:19][N:14]([C:13]3[CH:8]=[C:9]([NH2:24])[C:10]([NH2:21])=[CH:11][CH:12]=3)[CH2:15][CH2:16]2)[CH2:10][CH2:9][CH2:8][CH2:13]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 220408162-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine

Product 1

HCID 22040478HCID 22040478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A flame dried 2 L three necked round bottom flask purged with N2 was charged with LAH (2.32 g, 58.0 mmol) and dry THF (60 mL). The resulting suspension was cooled to 0° C. and a suspension of t-butyl ester 1 (10.0 g, 29.0 mmol) in dry THF (60 mL) was slowly added while keeping the internal reaction temperature under 5° C. Reaction stirred at 0° C. for 30 min followed by stirring at RT for 30 min. After the reaction was judged complete, the stirred reduction mixture was treated with successive dropwise addition of 2.3 mL H2O, 2.3 mL NaOH, and 7.2 mL H2O. Reaction mixture filtered through Celite, washed with ethyl acetate and methanol, and evaporated. Crude product absorbed onto silica gel and chromatographed using 97:3 CH2Cl2/MeOH to give 2 as an orange solid. 1H NMR (300 MHz, CDCl3) δ 8.40 (d, J=5.5 Hz, 1H), 8.05 (br s, 1H), 7.96 (d, J=2.75 Hz, 1H), 7.29 (d, J=2.75 Hz, 1H), 6.92 (d, J 9.35 Hz, 1H), 6.75 (m, 2H), 4.68 (s, 2H), 3.07 (d, J=5.23 Hz, 3H).

Workup

  1. dry with materialA flame dried 2 L three necked round bottom flask
  2. custompurged with N2
  3. additionwas slowly added
  4. customunder 5° C
  5. customReaction
  6. stirringby stirring at RT for 30 min
  7. customReaction mixture
  8. filtrationfiltered through Celite
  9. washwashed with ethyl acetate and methanol
  10. customevaporated
  11. customCrude product absorbed onto silica gel
  12. customchromatographed

Sources & evidence

ORD record
ord-2eb7bc06a12a44f2a07797f894c2bb9b
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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