Acetic Acid → HCID 59859907, compound

HRID 1944522Notes

Reaction equation

HRID 1944522 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:7])=[CH:4][CH:3]=1.[C:21]1([CH2:27][CH:28]=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.C(O)(=O)C>ClCCCl>[CH2:28]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:7])=[CH:19][CH:20]=1)[CH2:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 998PhenylacetaldehydeHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 43704708HCID 43704708, compound

Product 1

HCID 59859907HCID 59859907, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-amino-N-quinolin-3-yl-benzamide (1.0 g, 3.8 mmol), phenylacetaldehyde (0.49 mL, 4.18 mmol), tetramethylammonium triacetoxyborohydride (2.0 g, 7.60 mmol) and acetic acid (a catalytic amount) in 1,2-dichloroethane (40 mL) was heated at reflux for approximately 18 hours. The resultant solution was cooled to room temperature and washed with a saturated solution of aqueous sodium bicarbonate. The solution was applied to a flash silica gel column, and the product was eluted with ethyl acetate (40% to 75%) in hexane to give the product, 0.67 g (48%), as a colorless solid. MS: m/z 368 (MH+). 1H NMR (DMSO-d6): δ 2.88 (t, 2 H), 3.35 (t, 2 H), 6.51 (br t, 1 H), 6.7 (d, 2 H), 7.20-7.27 (m, 1 H), 7.30-7.33 (m, 4 H), 7.55-7.67 (m, 2 H), 7.87 (d, 2 H), 7.95 (m, 2 H), 8.82 (d, J=2 Hz, 1 H), 9.15 (d, J=2 Hz, 1H) and 10.25 (s, 1 H).

Workup

  1. temperatureat reflux for approximately 18 hours
  2. washwashed with a saturated solution of aqueous sodium bicarbonate
  3. washthe product was eluted with ethyl acetate (40% to 75%) in hexane
  4. customto give the product, 0.67 g (48%)

Sources & evidence

ORD record
ord-feb849a047d542efa3ec90169f80d549
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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