Hydrazine → 1'-(2-aminoethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 425713Notes

Reaction equation

HRID 425713 reaction equation
[O:1]=[C:2]1[C:10]2([C:14]3=[CH:15][C:16]4[O:20][CH2:19][O:18][C:17]=4[CH:21]=[C:13]3[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][CH2:23][N:24]1C(=O)C2C(=CC=CC=2)C1=O.NN>CO>[NH2:24][CH2:23][CH2:22][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]2([C:14]3=[CH:15][C:16]4[O:20][CH2:19][O:18][C:17]=4[CH:21]=[C:13]3[O:12][CH2:11]2)[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 592633552-[2-(2'-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-1'(2'H)-yl)ethyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 592633311'-(2-aminoethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneYield 56.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-[2-(2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)ethyl]-1H-isoindole-1,3(2H)-dione (20.0 g, 44.0 mmol) in methanol (400 mL) was added hydrazine (8.00 mL). The mixture was stirred at ambient temperature for 48 h and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to flash chromatography eluting with ethyl acetate/methanol/ammonia (10/1/0.2) to afford the crude product which was recrystalized from ethyl acetate to yield the title compound (8.0 g) in 56% yield as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.34 (m, 1H), 7.17 (dd, 1H), 7.06 (dd, 1H), 6.95 (d, 1H), 6.51 (s, 1H), 6.18 (s, 1H), 5.89-5.82-(ABq, 2H), 4.93 (d, 1H), 4.66 (d, 1H), 3.95-3.74-(m, 2H), 3.06 (t, 2H), 1.59-1.35-(br, 2H); 13C NMR (75 MHz, CDCl3) δ 178.0, 155.9, 148.8, 142.3, 132.4, 128.9, 124.0, 123.4, 119.5, 108.6, 103.1, 101.5, 93.6, 80.5, 58.2, 43.4, 39.8; MS (ES+) m/z 325 (M+1), 308 (M−16).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo to dryness
  3. washeluting with ethyl acetate/methanol/ammonia (10/1/0.2)
  4. customto afford the crude product which
  5. customwas recrystalized from ethyl acetate

Sources & evidence

ORD record
ord-dd54c2fc274940bd8c0073c41b2c560e
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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