Hydrochloric Acid → HCID 9901791, compound

HRID 1826988Notes

Reaction equation

HRID 1826988 reaction equation
NC1NC2C(C(C3C=CC=CC=3)C=1C#N)=CC=CC=2.[NH:20]=[C:21]1[C:30]([C:31]#[N:32])=[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=2)[C:28]2[C:23](=[CH:24][C:25]([O:41][CH3:42])=[CH:26][CH:27]=2)[S:22]1.[BH4-].[Na+].Cl>CO.CCOCC>[NH2:20][C:21]1[S:22][C:23]2[C:28]([CH:29]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=3)[C:30]=1[C:31]#[N:32])=[CH:27][CH:26]=[C:25]([O:41][CH3:42])[CH:24]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 9878158HCID 9878158, compoundHCID 9880202HCID 9880202, compound

Product 1

HCID 9901791HCID 9901791, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Amino-3-cyano-4-phenyl-1,4-dihydroquinoline: A solution of 2-imino-3-cyano-7-methoxy-4-(3′-methoxy-phenyl)-2H-thiochromene (25 mg, 0.077 mmol) in 2.3 mL of dry methanol was treated with sodium borohydride (5.0 mg, 0.13 mmol) at 0° C. The resultant mixture was stirred overnight at room temperature. It was then neutralized with 3 drops of a 1 N solution of hydrochloric acid, dissolved in 20 mL of ether, washed twice with 10 mL of aqueous saturated bicarbonate and dried with sodium sulfate. The solvent was evaporated and the residue was purified by flash chromatography using 25% ethyl acetate/hexanes to yield 15.9 mg (63%) of 2-amino-3-cyano-7-methoxy-4-(3-methoxyphenyl)-4H-thiochromene as a pale yellow solid. 1H NMR (CDCl3): 7.14–7.21 (m, 2H), 6.79–6.82 (m, 3H), 6.72–6.76 (m, 2H), 4.82 (s, 1H), 4.66 (brs, 2H), 3.79 (s, 3H), 3.75 (s, 3H).

Workup

  1. washwashed twice with 10 mL of aqueous saturated bicarbonate
  2. dry with materialdried with sodium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ce27475bf8e94dab93dee39ced77f37d
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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