Sodium Cyanate → HCID 14626170, compound

HRID 1638705Notes

Reaction equation

HRID 1638705 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH3:16])=[N:4][C:3]=1[O:17][C:18](=[O:24])[N:19]([CH2:22][CH3:23])[CH2:20][CH3:21].[O-:25][C:26]#[N:27].[Na+]>C(O)(=O)C>[CH2:20]([N:19]([CH2:22][CH3:23])[C:18]([O:17][C:3]1[N:4]=[C:5]([CH3:16])[C:6]2[C:11]([C:2]=1[NH:1][C:26]([NH2:27])=[O:25])=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)=[O:24])[CH3:21]

Participants

4

Reactant 2

HCID 517096Sodium CyanateHCID 14626125HCID 14626125, compound

Product 1

HCID 14626170HCID 14626170, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-amino-3-(diethylcarbamyloxy)-6,7-dimethoxy-1-methylisoquinoline (1.0 g, 3 mmol) in acetic acid (10 mL) was added sodium cyanate (0.23 g, 3.6 mmol) and the mixture was stirred under nitrogen at room temperature for 72 hours. Then the mixture was evaporated to dryness in vacuo and the residue triturated with water to give a gelatinous precipitate which was collected (0.69 g). The filtrate gave additional solids (0.50 g). The combined solids were dissolved in chloroform and purified by low pressure column chromatography on a silica gel column. Elution with 1.8% methanol/chloroform gave purified title compound which was collected from methylene chloride/ether as a colorless crystalline solid (0.865 g, 68.7%), mp 215°-216° C. IR (KBr): 3323, 3316, 3313, 3199, 1712, 1697, 1667, 1428 cm-1 ; NMR (CDCl3): δ 1.23 and 1.28 [each t, J=7 Hz, total 6H, N(CH2CH3)2 ], 2.80 (s, 3H, 1-CH3), 3.20-3.70 [br m, 4H, N(CH2CH3)2 ], 4.98 (s, 2H, NHCONH2), 6.78 and 7.01 (two s, each 1H, 5,8-H), 6.876 (br s, 1H, 4-NH). MS (DCI): 377 (MH)+ ; UV (EtOH) nm: 247 (ε51600), 275 (ε4800), 287 (ε5050), 297 (ε5000).

Workup

  1. customThen the mixture was evaporated to dryness in vacuo
  2. customthe residue triturated with water
  3. customto give a gelatinous precipitate which
  4. customwas collected (0.69 g)

Sources & evidence

ORD record
ord-74c071491d724ad787e2fa6eb6a22189
Source dataset
uspto-grants-1989_11
Patent number
US04880817

Reaction notes

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