Sodium Hydroxide → HCID 59161236, compound

HRID 545517Notes

Reaction equation

HRID 545517 reaction equation
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-])=O)[C:15]1[CH2:14][CH2:13][CH:12]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH2:11][C:10]2=1.[OH-].[Na+]>C(O)C.Cl>[NH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][N:16]1[C:15]2[CH2:14][CH2:13][CH:12]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH2:11][C:10]=2[C:9]2[C:17]1=[CH:18][CH:19]=[C:7]([Cl:6])[CH:8]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 59161192HCID 59161192, compound

Product 1

HCID 59161236HCID 59161236, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Dissolve tin(II) chloride dihydrate (2.15 g, 9.5 mmol) in absolute ethanol (10 mL) and add it to N-[6-chloro-9-(2-nitro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 104) (810 mg, 1.9 mmol) in concentrated hydrochloric acid (10 mL). Heat the reaction at 60° C. for 1.5 h. Allow to cool and add 5N NaOH (27 mL) until pH=11-12. Extract the suspended solids into ethyl acetate (4×). Combine the organic portions and wash with water, brine, dry (MgSO4), and concentrate in vacuo to obtain a solid. Pass over a silica pad eluting with 25% ethyl acetate/dichloromethane to obtain 640 mg (85%). MS (ES): m/z 396, 398 (M+1), 394 (M−1); 1H NMR(DMSO-d6): δ 7.86 (d, 1H, J=7.5 Hz), 7.49 (d, 1H, J=1.8 Hz), 7.24 (d, 1H, J=8.8 Hz), 7.04 (dd, 1H, J=8.6, 2.0 Hz), 6.93 (dt, 1H, J=7.5, 1.3 Hz), 6.71 (dd, 1H, J=8.1, 1.1 Hz), 6.37 (dt, 1H, J=7.5, 1.3 Hz), 5.89 (d, 1H, J=7.0 Hz), 5.14 (m, 4H), 4.03 (m, 1H), 2.98 (dd, 1H, J=15.2, 5.1 Hz), 2.75-2.60 (m, 2H), 2.55 (m, 1H), 2.41 (m, 1H), 1.97 (m, 1H), 1.81 (m, 1H), 1.03 (d, 3H, J=4.0 Hz), 1.02 (d, 3H, J=4.4 Hz).

Workup

  1. temperatureHeat
  2. customthe reaction at 60° C. for 1.5 h
  3. temperatureto cool
  4. extractionExtract the suspended solids into ethyl acetate (4×)
  5. washCombine the organic portions and wash with water, brine
  6. dry with materialdry (MgSO4)
  7. concentrationconcentrate in vacuo
  8. customto obtain a solid
  9. washPass over a silica pad eluting with 25% ethyl acetate/dichloromethane
  10. customto obtain 640 mg (85%)

Sources & evidence

ORD record
ord-281a49e1bc154aaaaa8e8b83cf3182ce
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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