Hydrochloric Acid → HCID 18782137, compound

HRID 1420557Notes

Reaction equation

HRID 1420557 reaction equation
[Na].Cl.[Cl:3][CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[N:7]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:6]1.[CH2:29]=O>CO.C1COCC1>[Cl:3][CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]([CH3:29])[CH2:15][C:16]3[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)=[CH:11][CH:12]=2)[N:7]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5360545SodiumHCID 18782123HCID 18782123, compound

Product 1

HCID 18782137HCID 18782137, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium cyanoborohydnide (40 mg, 0.64 mmol) then 2N HCl (0.5 mL) were added to a solution of 30 (96 mg, 0.24 mmol) and formaldehyde (0.18 mL of a 40% w/v aq. solution, 2.4 mmol) in MeOH (15 mL) and THF (5 mL) and the mixture stirred at 20° C. for 45 min. The solvent was evaporated, the residue was diluted with water and extracted with CH2Cl2 (×2), and the extracts dried (Na2SO4) and evaporated. Dry column chromatography (eluting with 1:2 EtOAc:petroleum ether) gave 3-(chloromethyl)-1-(methanesulfonyl)-6-[N-methyl-N-(4-nitrobenzyl)amino]indoline (31) (73 mg, 73%), mp (benzene-petroleum ether) 138-139 C. 1H NMR (CDCl3) a 8.18 (d, J=8.8 Hz, 2 H, ArH o to NO2), 7.39 (d, J=8.8 Hz, 2 H, ArH m to NO2), 7.05 (d, J=8.4 Hz, 1 H, H-4), 6.82 (d, J=2.4 Hz, 1 H, H-7), 6.3 5 (dd, J=8.4 2.4 Hz, 1 H, H-5), 4.63 (s, 2 H, NCH2Ar), 4.04 (dd, J=10.8, 8.8 Hz, 1 H, CHHN), 3.93 (dd, J=10.8, 4.7 Hz, 1 H, CHHN), 3.71 (dd, J=10.4, 4.1 Hz, 1 H, CHHCl), 3.68-3.61 (m, 1 H, H-3), 3.55 (dd, J=10.4, 7.8 Hz, 1 H, CHHCl), 3.11 (s, 3 H, NCH3), 2.81 (s, 3 H, NSO2CH3). 13C NMR a 150.3, 147.1, 146.5, 143.5, 118.9 (C-6,8,9,1,4), 127.4, 123.9 (C-2 and 6, 3 and 5), 125.5, 107.7, 97.9 (C-4,5,7), 56.5, 54.7 (C-2, NCH2Ar), 46.9 (CH2Cl), 41.8 (C-3), 39.5 (NCH3), 34.5 (SO2CH3). Anal. Calculated for C18H20ClN3O4S): C, 52.8; H, 4.9; N, 10.3; Cl, 8.7. Found: C, 52.6; H 5.1; N, 10.1; Cl, 8.9%.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water
  3. extractionextracted with CH2Cl2 (×2)
  4. dry with materialthe extracts dried (Na2SO4)
  5. customevaporated
  6. customDry
  7. washcolumn chromatography (eluting with 1:2 EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-938c7e02e2cd476fb0e3465088e136b0
Source dataset
uspto-grants-2000_06
Patent number
US06071908

Reaction notes

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