Ammonia → HCID 10674507, compound

HRID 1456872Notes

Reaction equation

HRID 1456872 reaction equation
CO[C:3](=O)[C:4]#[C:5][CH2:6]O.[N:9]1[C:18]2[C:13](=CC=CC=2)[CH:12]=[CH:11][C:10]=1[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]3[CH:51]=[CH:50][C:49]4[C:44](=CC=CC=4)[N:43]=3)=[CH:36][CH:35]=2)(C)[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:23][CH:22]=1.N.[OH2:53]>>[N:43]1[C:44]2[C:49](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:50]=[CH:51][C:42]=1[CH2:41][O:40][C:37]1[CH:38]=[CH:39][C:34]([C:27]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:10]3[CH:11]=[CH:12][C:13]4[C:18](=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:9]=3)=[CH:22][CH:23]=2)([OH:53])[C:28]#[C:29][C:30]([OH:32])=[O:31])=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 325086Methyl 4-hydroxybut-2-ynoateHCID 9850972HCID 9850972, compound

Product 1

HCID 10674507HCID 10674507, compound

Procedure

The desired compound was prepared according to the method of Example 1, step 3, except substituting 4,4-bis(2-quinolylmethoxy)phenyl)-4-hydroxy-2-butynoic acid methyl ester, prepared as in step 1, for 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentanoic acid: mp 169°-172° C.; 1H NMR (300 MHz, DMSO-d6) d 5.35 (s, 4H), 7.04 (d, 4H, J=9 Hz), 7.37 (d, 4H, J=9 Hz), 7.63 (m, 4H), 7.78 (m, 2H), 8.00 (m, 4H), 8.40 (d, 2H, J=8 Hz), 13.75 (bs, 1H); MS (DCl--NH3) m/e: 567 (M+H)+. Anal. Calc'd. for C36H26 N2O4.0.5 H2O: C, 75.12; H, 4.73; N, 4.89. Found: 75.19; H, 4.80; N, 4.60.

Sources & evidence

ORD record
ord-4b38b0d1aaba4cf1b4128b9a206fd579
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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